1,2-Dichloroethane → tert-Butyl (4S)-4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylate

HRID 451301ノート

反応式

HRID 451301 の反応式
[C:1]1([CH2:7][O:8][N:9]2[C:15](=[O:16])[N:14]3[CH2:17][C@H:10]2[CH2:11][CH2:12][C@H:13]3[C:18]([OH:20])=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[NH2:21][C@H:22]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:23]1.C(N(CC)CC)C.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>ClCCl>[CH2:7]([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:21][C@H:22]1[CH2:28][CH2:27][CH2:26][N:25]([C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:24][CH2:23]1)=[O:20])[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

7

反応物 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 32639843(S)-tert-butyl 4-aminoazepane-1-carboxylateHCID 57389355(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid

生成物 1

HCID 86659585tert-Butyl (4S)-4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)azepane-1-carboxylate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (2S,5R)-6-(phenylmethoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid (51.7 mg, 0.187 mmol) in dry dichloromethane (2 mL) was added a solution of tert-butyl (4S)-4-aminoazepane-1-carboxylate (69 mg, 0.275 mmol), triethylamine (0.090 mL, 0.646 mmol), HOBT (42.5 mg, 0.278 mmol), and EDC (54.7 mg, 0.285 mmol) sequentially at room temperature under nitrogen. The reaction was stirred at room temperature overnight. The reaction mixture was concentrated under vacuum and the residue was purified by HPLC on a 30×100 mm Waters Sunfire column eluted with 15% to 100% CH3CN+0.05% TFA/water+0.05% TFA over 15 minutes to afford the title compound as a white solid after lyophilization.

後処理

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by HPLC on a 30×100 mm Waters Sunfire column
  3. washeluted with 15% to 100% CH3CN+0.05% TFA/water+0.05% TFA over 15 minutes

出典と根拠

ORDレコード
ord-311c58bf7b6249ee9b290c560de9e962
出典データセット
uspto-grants-2013_07
特許番号
US08487093B2

反応ノート

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