Z-THR(TBU)-OH synthesis
- Product Name:Z-THR(TBU)-OH
- CAS Number:16966-09-9
- Molecular formula:C16H23NO5
- Molecular Weight:309.36
52785-41-8
16966-09-9
The general procedure for the synthesis of (2S,3R)-2-(((benzyloxy)carbonyl)amino)-3-(tert-butoxy)butanoic acid from linaclotide impurity 23 was as follows: z-Thr(tBu)-OMe (169 g) was added to a 2 L beaker with 300 mL of acetone and 600 mL of 1,2-dichloroethane, and the pH was adjusted to 10-11 with 1 M sodium hydroxide solution. After completion of the reaction, the reaction was washed once with 500 mL of ether, 800 mL of ethyl acetate was added, and the pH was adjusted to 2-3 with aqueous citric acid solution.Subsequently, the reaction was washed with 300 mL of water, and then with 300 mL of saturated brine. The organic phase was dried over 100 g of anhydrous sodium sulfate, filtered and concentrated under reduced pressure. To the residue was added 500 mL of ether and dried to obtain Z-Thr(tBu)-OH (130 g) in granular form in 80.3% yield.
52785-41-8
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16966-09-9
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Yield: 80.3%
Reaction Conditions:
with sodium hydroxide in water;acetone; pH=10 - 11
Steps:
1.4
4The Z-thr (tbu) -ome 169g was added to 2L beaker, 300Ml of acetone 600Ml, 2mlc / l sodium hydroxide adjusted to pH 10-11 reaction. The reaction is completed, washed with ether 500ml once, add ethyl acetate 800ml, citric acid aqueous solution to adjust the pH in 2-3.300ml washed, 300ml saturated salt water wash. 100G dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to dry granulated ether 500ML to give z-thr (tbu) -oH 130 g, yield 80.3%
References:
Jier Biochemical (Shanghai) Co., Ltd.;Liu Hao;Xu Hongyan CN106631900, 2017, A Location in patent:Paragraph 0015
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