Ether hydrochloride → (S)-2-amino-3-difluoromethoxypropionic acid benzyl ester hydrochloride salt

HRID 61291

반응식

HRID 61291 반응식
[CH2:1]([O:8][C:9](=[O:24])[C@@H:10]([NH:16]C(OC(C)(C)C)=O)[CH2:11][O:12][CH:13]([F:15])[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[ClH:25].CCOCC>CCOCC>[ClH:25].[CH2:1]([O:8][C:9](=[O:24])[C@@H:10]([NH2:16])[CH2:11][O:12][CH:13]([F:15])[F:14])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

4

반응물 2

HCID 10953452Ether hydrochlorideHCID 90041473(S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester

생성물 1

HCID 90040140(S)-2-amino-3-difluoromethoxypropionic acid benzyl ester hydrochloride salt수율 69%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

반응 조건

온도
0 °C

실험 절차

A solution of the compound of Formula XIII(a), (S)-2-tert-butoxycarbonylamino-3-difluoromethoxy-propionic acid benzyl ester (2.11 g, 5.89 mmol) in ether (10 mL) was treated with 2M HCl/ether, and stirred at 0° C. for 2 hours. The reaction mixture was concentrated to dryness and triturated with hexane/ether to give the compound of Formula V(a) (S)-2-amino-3-difluoromethoxy-propionic acid benzyl ester hydrochloride salt (1.15 g, 69%) as a white powder. 1H NMR (300 MHz, CDCl3): δ (ppm) 7.40-7.33 (m, 5H), 6.53 (broad s, 1H), 6.18 (wt, 1H), 5.25 (dd, 1H), 5.21 (dd, 2H), 4.53 (dt, 1H) 4.18 (td, 1H), 4.16-4.13 (m, 2H).

후처리

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customtriturated with hexane/ether

출처 및 근거

ORD 기록
ord-53d4b22b70ed40a481fbf2687825441d
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09441012B2

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