ChemicalBook CAS DataBase List Fmoc-Val-Ala-PAB-OH

Fmoc-Val-Ala-PAB-OH synthesis

6synthesis methods

Product Name:Fmoc-Val-Ala-PAB-OH
CAS Number:1394238-91-5
Molecular formula:C30H33N3O5
Molecular Weight:515.6

150114-97-9
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623-04-1 Synthesis

623-04-1
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1394238-91-5
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$56.00/10mg

Yield: 100%

Reaction Conditions:

with N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline in methanol;dichloromethane at 20; for 26 h;

Steps:

Compound 21: (9H-fluoren-9-yl)methyl ((S)-1 -(((S)-1 -((4-(hydroxymethyl)phenyl)-amino)-1 -oxopropan-2-yl)amino)-3-methyl-1 -oxobutan-2-yl)carbamate
To a solution of Fmoc-Val-Ala-OH (CAS number [150114-97-9], 1 g, 2.44 mmol) in DCM (30 mL) and MeOH (15 mL) were added 4-aminobenzyl alcohol (612 mg, 4.87 mmol) and EEDQ (1 .22 g, 4.87 mmol). The reaction medium was stirred at RT for 24 h then additional 4-aminobenzyl alcohol (612 mg, 4.87 mmol) and EEDQ (1 .22 g, 4.87 mmol) were added and the stirring carried on 2 h. The reaction medium was then concentrated in vacuo; Et20 was added to the crude product, the mixture wasstirred and filtered to give a brown solid that was diluted in Et20 and the mixture was stirred at RT overnight. It was then filtered and the precipitate was dried to give 1 .3 g of compound 21 as a brown solid (quant.).RMN 1H (400 MHz, ? in ppm, DMSO-d6): 0.86 (d, J = 7.0 Hz, 3 H); 0.89 (d, J =7.0 Hz, 3 H); 1.30 (d, J = 7.0 Hz, 3 H); 2.00 (m, 1 H); 3.91 (m, 1 H); 4.19 to 4.34 (m,4 H); 4.43 (d, J = 5.7 Hz, 2 H); 5.08 (t, J = 5.7 Hz, 1 H); 7.23 (d, J = 7.9 Hz, 2 H); 7.31(t, J = 7.9 Hz, 2 H); 7.40 (m, 3 H); 7.53 (d, J = 9.1 Hz, 2 H); 7.73 (t, J = 8.6 Hz, 2 H);7.89 (d, J = 7.9 Hz, 2 H); 8.16 (d, J = 7.3 Hz, 1 H); 9.91 (5, 1 H). LCMS (A): ES m/z =292; m/z = 393; m/z = 516 [Mi-H] tR = 1.21 mm.

References:

SANOFI;BOUCHARD, Hervé;BRUN, Marie-Priscille;HUBERT, Philippe WO2018/206635, 2018, A1 Location in patent:Page/Page column 179; 180