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

HRID 44142

반응식

HRID 44142 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-a3500c0216c449f7981b9331224c5b24
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541363B2

연결된 노트

불러오는 중…