Diisopropylethylamine → [(S)-1-(Methoxy-methyl-carbamoyl)-2-methyl-propyl]carbamic acid benzyl ester

HRID 44142

反応式

HRID 44142 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]([CH:16]([CH3:18])[CH3:17])[C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.[CH3:20][O:21]CN.CCN=C=NCCC[N:32]([CH3:34])C.Cl.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@H:12]([C:13](=[O:15])[N:32]([O:21][CH3:20])[CH3:34])[CH:16]([CH3:18])[CH3:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 726987N-Carbobenzoxy-L-valineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 21959107Methoxymethanamine hydrochloride

生成物 1

HCID 10469699[(S)-1-(Methoxy-methyl-carbamoyl)-2-methyl-propyl]carbamic acid benzyl ester収率 87.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

To (S)-2-benzyloxycarbonylamino-3-methyl-butyric acid (7) (50.0 g, 199 mmol), N-methoxymethylamine hydrochloride (38.8 g, 398 mmol) and EDC.HCl (47.7 g, 249 mmol) in DCM (500 mL) was added DIPEA (87 mL, 497 mmol) and the reaction mixture stirred at ambient temperature for 20 h, after which time the reaction mixture was diluted with DCM (200 mL), washed with 1M HCl (aq) (3×200 mL), 1M NaOH (aq) (200 mL), sat. NaHCO3 (aq) (200 mL) and brine (300 mL). The organic layer was dried over MgSO4, filtered and the solvent removed under vacuum to give the desired compound as a colourless oil (51.2 g, 87%); (AnalpH2_MeOH—4 min) Rt 2.76 min; m/z 295 (MH)+.

後処理

  1. washwashed with 1M HCl (aq) (3×200 mL), 1M NaOH (aq) (200 mL), sat. NaHCO3 (aq) (200 mL) and brine (300 mL)
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-a3500c0216c449f7981b9331224c5b24
出典データセット
uspto-grants-2013_09
特許番号
US08541363B2

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