Acetic Acid → (2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide

HRID 627257노트

반응식

HRID 627257 반응식
[CH2:1]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[C:11]([CH2:21][CH2:22][N+:23]([O-])=O)=[CH:12][C@H:13]2[C:18]([NH2:20])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:26](O)(=[O:28])[CH3:27].CCN(C(C)C)C(C)C.C(OC(=O)C)(=O)C>C(O)C.C(Cl)Cl.[Zn]>[C:26]([NH:23][CH2:22][CH2:21][C:11]1[C@@H:10]2[CH2:17][N:14]([C:15](=[O:16])[N:9]2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C@H:13]([C:18]([NH2:20])=[O:19])[CH:12]=1)(=[O:28])[CH3:27]

참가 물질

8

반응물 4

HCID 176Acetic AcidHCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 89853135(2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide2회

생성물 1

HCID 89863102(2S,5R)-4-(2-acetamidoethyl)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide수율 99.4%

시약·촉매·용매 3

HCID 23994Zinc촉매HCID 702Ethanol용매HCID 6344Dichloromethane용매

실험 절차

To a solution of (2S,5R)-6-(benzyloxy)-4-(2-nitroethyl)-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-ene-2-carboxamide (Intermediate 226, 0.300 g, 0.87 mmol) in ethanol (10 mL) was added zinc dust (1.416 g, 21.66 mmol) and acetic acid (1.984 mL, 34.65 mmol). The reaction mixture was stirred at ambient temperature for 1 hour. Then DIPEA (2.118 mL, 12.13 mmol) was added to reaction mixture followed by acetic anhydride (0.245 mL, 2.60 mmol). The reaction mixture was stirred for an additional 2 hours, then diluted with DCM, washed with saturated bicarbonate and concentrated to dryness. Flash chromatography, 0%-10% MeOH/DCM, afforded the title compound as a clear oil (0.31 g, 61%).

후처리

  1. stirringThe reaction mixture was stirred for an additional 2 hours
  2. washwashed with saturated bicarbonate
  3. concentrationconcentrated to dryness

출처 및 근거

ORD 기록
ord-8111aa82e42d4b2bab1158e5e0716f91
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309245B2

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