1-Hydroxybenzotriazole → 2-{(S)-2-[2-benzyloxycarbonylamino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester

HRID 2222983

반응식

HRID 2222983 반응식
[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:21])[C@@H:12]([NH2:20])[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4].[CH2:22]([O:29][C:30]([NH:32][CH:33]([C:37]1[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([CH3:45])[CH:38]=1)[C:34](O)=[O:35])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(N(C(C)C)CC)(C)C.ON1C2C=CC=CC=2N=N1.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O>[CH3:1][O:2][C:3]([C:5]1[N:6]=[C:7]([NH:10][C:11](=[O:21])[C@@H:12]([NH:20][C:34](=[O:35])[CH:33]([NH:32][C:30]([O:29][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:31])[C:37]2[CH:42]=[CH:41][C:40]([O:43][CH3:44])=[C:39]([CH3:45])[CH:38]=2)[CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[S:8][CH:9]=1)=[O:4]

참가 물질

7

반응물 5

HCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 130500O-benzotriazol-1-yl-tetramethyluroniumHCID 68798586Benzyloxycarbonylamino-(4-methoxy-3-methyl-phenyl)-acetic acidHCID 866040402-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester

생성물 1

HCID 866040582-{(S)-2-[2-benzyloxycarbonylamino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester수율 69.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
0 °C

실험 절차

To a solution of 2-((S)-2-amino-3-phenyl-propionylamino)-thiazole-4-carboxylic acid methyl ester (0.93 g, 3.04 mmol), benzyloxycarbonylamino-(4-methoxy-3-methyl-phenyl)-acetic acid (1.0 g, 3.04 mmol), diisopropylethylamine (2.1 mL, 12 mmol) and 1-hydroxybenzotriazole (0.46 g, 3.04 mmol) in N,N-dimethylformamide (10 mL) at 0° C. was added O-benzotriazol-1-yl-N,N, N′,N′-tetramethyluronium hexaflurorophosphate (1.15 g, 3.04 mmol). The reaction mixture was stirred at 0° C. for 2 hours. The reaction mixture was poured into ice water and extracted with ethyl acetate. The organic layer was separated, washed with water, brine, dried over sodium sulfate and concentrated. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give 2-{(S)-2-[2-benzyloxycarbonylamino-2-(4-methoxy-3-methyl-phenyl)-acetylamino]-3-phenyl-propionylamino}-thiazole-4-carboxylic acid methyl ester as a white solid (1.3 g, 69%).

후처리

  1. extractionextracted with ethyl acetate
  2. customThe organic layer was separated
  3. washwashed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography over silica gel
  7. washeluted with 2:1 ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-4b1de5cdc0af479d9c55e082234a0818
출처 데이터셋
uspto-grants-2008_05
특허 번호
US07371869B2

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