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

HRID 627257ノート

反応式

HRID 627257 の反応式
[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]

参加物

8

反応物 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-carboxamide2 回

生成物 1

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

試薬・触媒・溶媒 3

HCID 23994Zinc触媒HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

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

出典と根拠

ORDレコード
ord-8111aa82e42d4b2bab1158e5e0716f91
出典データセット
uspto-grants-2016_04
特許番号
US09309245B2

反応ノート

読み込み中…