1,2-Dichloroethane → {(S)-6-Oxo-7-[2-(2,2,3,3,3-pentafluoro-propylcarbamoyl)-propionylamino]-6,7-dihydro-dibenzo[b,d]azepin-5-yl}-acetic acid methyl ester

HRID 30994노트

반응식

HRID 30994 반응식
[CH3:1][O:2][C:3](=[O:22])[CH2:4][N:5]1[C:11](=[O:12])[C@@H:10]([NH2:13])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[C:7]2[CH:18]=[CH:19][CH:20]=[CH:21][C:6]1=2.[CH3:23][CH:24]([C:28]([NH:30][CH2:31][C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])=[O:29])[C:25](O)=[O:26].ON1C2C=CC=CC=2N=N1.C(N(C(C)C)C(C)C)C.C(Cl)CCl>C1COCC1>[CH3:1][O:2][C:3](=[O:22])[CH2:4][N:5]1[C:11](=[O:12])[C@@H:10]([NH:13][C:25](=[O:26])[CH:24]([C:28](=[O:29])[NH:30][CH2:31][C:32]([F:37])([F:38])[C:33]([F:34])([F:36])[F:35])[CH3:23])[C:9]2[CH:14]=[CH:15][CH:16]=[CH:17][C:8]=2[C:7]2[CH:18]=[CH:19][CH:20]=[CH:21][C:6]1=2

참가 물질

7

반응물 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 210724942-Methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acidHCID 58972470HCID 58972470, 화합물

생성물 1

HCID 58972529{(S)-6-Oxo-7-[2-(2,2,3,3,3-pentafluoro-propylcarbamoyl)-propionylamino]-6,7-dihydro-dibenzo[b,d]azepin-5-yl}-acetic acid methyl ester수율 70%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

((S)-7-Amino-6-oxo-6,7-dihydro-dibenzo[b,d]azepin-5-yl)-acetic acid methyl ester (25 mg, 0.85 mmol) were dissolved in THF and subsequently treated with 2-methyl-N-(2,2,3,3,3-pentafluoro-propyl)-malonamic acid (25 mg, 0.1 mmol), 1-hydroxybenzotriazole (11.6 mg, 0.85 mmol), N-ethyldiisopropylamine (0.03 ml, 0.17 mmol) and EDC (16.5 mg, 0.85 mmol). After stirring for 2.5 h at ambient temperature, the reaction mixture is quenched with water and extracted with ethyl acetate. The aqueous phase is extracted twice with ethyl acetate and the combined organic layers are extracted with water (2×5 ml) and saturated aqueous sodium chloride (5 ml), combined, dried over anhydrous sodium sulfate and evaporated to dryness. Chromatography (silica, eluent cyclohexane/ethyl acetate 65/35) afforded the product as colorless solid (70%). MS: m/e=528 (M+H+).

후처리

  1. customthe reaction mixture is quenched with water
  2. extractionextracted with ethyl acetate
  3. extractionThe aqueous phase is extracted twice with ethyl acetate
  4. extractionthe combined organic layers are extracted with water (2×5 ml) and saturated aqueous sodium chloride (5 ml)
  5. dry with materialdried over anhydrous sodium sulfate
  6. customevaporated to dryness

출처 및 근거

ORD 기록
ord-3a579f662dd540eb8ed3cb244c79d21b
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07425551B2

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