Formic Acid → 2-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

HRID 2222984노트

반응식

HRID 2222984 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:44])[C@@H:12]([NH:20][C:21](=[O:43])[CH:22]([NH:32]C(OCC2C=CC=CC=2)=O)[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH3:31])[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].C(O)=O>CO.[Pd]>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:44])[C@@H:12]([NH:20][C:21](=[O:43])[CH:22]([NH2:32])[C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[C:25]([CH3:31])[CH:24]=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

5

반응물 2

HCID 284Formic AcidHCID 866040582-{(S)-2-[2-benzyloxycarbonylamino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

생성물 1

HCID 866040592-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 887Methanol용매

실험 절차

To a solution of 2-{(S)-2-[2-benzyloxycarbonylamino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester (1.0 g, 1.62 mmol) in methanol (40 mL) was added formic acid (4 g, 87 mmol). The solution was then degassed with nitrogen for 10 minute, followed by the addition of palladium black (1 g, 9.4 mmol). The reaction mixture was stirred at room temperature under nitrogen for 0.5 hours. The reaction mixture was filtered through a short pad of celite and the filtrate was concentrated to dryness. The residue was neutralized with saturated aqueous sodium bicarbonate solution and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate and concentrated to give crude 2-{(S)-2-[2-amino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as an off white foam (0.73 g, 93%).

후처리

  1. customThe solution was then degassed with nitrogen for 10 minute
  2. filtrationThe reaction mixture was filtered through a short pad of celite
  3. concentrationthe filtrate was concentrated to dryness
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined organic extracts were dried over sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2e87d40d169f40b080a5ec56982b3116
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371869B2

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