Trifluoroacetic acid → 2-((S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

HRID 2222979노트

반응식

HRID 2222979 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:47])[C@@H:12]([NH:20][C:21](=[O:46])[C@H:22]([NH:38]C(OC(C)(C)C)=O)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][C@H:31]3[CH2:35][O:34]C(C)(C)[O:32]3)=[CH:25][CH:24]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].FC(F)(F)C(O)=O>ClCCl>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:47])[C@@H:12]([NH:20][C:21](=[O:46])[C@H:22]([NH2:38])[C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][C@H:31]([OH:32])[CH2:35][OH:34])=[CH:27][CH:28]=2)[CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[S:8][CH:9]=1)=[O:4]

참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 866040552-((S)-2-{(R)-2-tert-butoxycarbonylamino-2-[4-((S)-2,2-dimethyl-[1,3]dioxolan4-ylmethoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

생성물 1

HCID 866040562-((S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester수율 90.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-((S)-2-{(R)-2-tert-butoxycarbonylamino-2-[4-((S)-2,2-dimethyl-[1,3]dioxolan4-ylmethoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (170 mg, 0.25 mmol) in dichloromethane (2.0 mL) was added trifluoroacetic acid (0.5 mL, 6.5 mmol) at 0° C. The reaction was warmed to room temperature and stirred for 4 hours. The solvent was removed under vacuum and the residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution. The aqueous layer was extracted with ethyl acetate and the extracts were combined, washed with brine and dried over sodium sulfate to give 2-((S)-2-{(R)-2-amino-2-[4-((R)-2,3-dihydroxy-propoxy)-phenyl]-acetylamino}-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester as a foam (120 mg, 90%).

후처리

  1. customThe solvent was removed under vacuum
  2. customthe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate solution
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate

출처 및 근거

ORD 기록
ord-339f6136853f4b69b4b6cf2a9275658d
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371869B2

반응 노트

불러오는 중…