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| | (S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE Basic information |
| Product Name: | (S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE | | Synonyms: | (S)-(-)-3-BOC-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE;(S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE;(S)-N-BOC-2,2-DIMETHYLOXAZOLINDINE-4-CARBOXYLIC ACID METHYL ESTER;2,2-DIMETHYL OXAZOLIDINE-3,4-DICARBOXYLIC ACID 3-TERT-BUTYL ESTER 4-METHYL ESTER;3-(1,1-DIMETHYLETHYL)-4-METHYL-(S)-2,2-DIMETHYL-3,4-OXAZOLIDINE CARBOXYLATE;3-(1,1-DIMETHYLETHYL)-4-METHYL-(S)-2,2-DIMETHYL-3,4-OXAZOLIDINEDICARBOXYLATE;3,4-Oxazolidinedicarboxylic acid, 2,2-diMethyl-, 3-(1,1-diMethylethyl) 4-Methyl ester, (4S)-;(S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE-2 | | CAS: | 108149-60-6 | | MF: | C12H21NO5 | | MW: | 259.3 | | EINECS: | | | Product Categories: | Chiral Building Blocks;Esters (Chiral);Synthetic Organic Chemistry | | Mol File: | 108149-60-6.mol |  |
| | (S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE Chemical Properties |
| Boiling point | 101-102 °C2 mm Hg(lit.) | | density | 1.082 g/mL at 25 °C(lit.) | | refractive index | n20/D 1.443(lit.) | | Fp | 199 °F | | storage temp. | Keep in dark place,Sealed in dry,Room Temperature | | form | Liquid | | pka | -3.58±0.60(Predicted) | | color | Clear yellow | | Optical Rotation | [α]20/D 55°, c = 1.3 in chloroform | | InChI | 1S/C12H21NO5/c1-11(2,3)18-10(15)13-8(9(14)16-6)7-17-12(13,4)5/h8H,7H2,1-6H3/t8-/m0/s1 | | InChIKey | ZNBUXTFASGDVCL-QMMMGPOBSA-N | | SMILES | COC(=O)[C@@H]1COC(C)(C)N1C(=O)OC(C)(C)C | | CAS DataBase Reference | 108149-60-6(CAS DataBase Reference) |
| Hazard Codes | Xi | | Risk Statements | 36/37/38 | | Safety Statements | 26-36-37/39 | | RIDADR | NA 1993 / PGIII | | WGK Germany | 3 | | HS Code | 29349990 | | Storage Class | 10 - Combustible liquids | | Hazard Classifications | Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| | (S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE Usage And Synthesis |
| Chemical Properties | Clear yellow liquid | | Uses | (S)-(-)-3-tert-Butoxycarbonyl-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine is a useful intermediate used in the improved synthesis of Garner′s aldehyde and analogs with multiple pharmaceutical applications. | | Synthesis | To a solution of Boc-L-serine methyl ester (2a, 1.94 g, 8.85 mmol, 1.00 eq.) in dichloromethane (20.0 mL) was added 2,2-dimethoxypropane (3.25 mL, 26.6 mmol, 3.00 eq.) and boron trifluoride-ether complex (0.0553 mL, 0.443 mmol, 0.500 equivalent) in a dilute solution in dichloromethane (15.0 mL). The reaction mixture was stirred at 25 °C for 3 h and then quenched with saturated aqueous NaHCO3 solution. The aqueous layer was extracted with two portions of ethyl acetate. The combined organic layers were washed with 10% NaCl aqueous solution, dried with Na2SO4, filtered, and concentrated in vacuum. Purification of the residue by silica gel column chromatography (16% hexane solution of ethyl acetate) afforded (R)-(-)-3-BOC-4-methoxycarbonyl-2,2-dimethyl-1,3-oxazolidine (2.28 g, 8.79 mmol, 99%) as a colorless oil. | | References | [1] Beilstein Journal of Organic Chemistry, 2017, vol. 13, p. 106 - 110
[2] Tetrahedron Letters, 1999, vol. 40, # 1, p. 113 - 116
[3] European Journal of Organic Chemistry, 2017, vol. 2017, # 6, p. 1045 - 1051
[4] Patent: WO2015/156601, 2015, A1. Location in patent: Page/Page column 23; 24; 25
[5] Organic Letters, 2003, vol. 5, # 23, p. 4253 - 4256 |
| | (S)-(-)-3-TERT-BUTOXYCARBONYL-4-METHOXYCARBONYL-2,2-DIMETHYL-1,3-OXAZOLIDINE Preparation Products And Raw materials |
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