Benzylamine → (3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide

HRID 419385노트

반응식

HRID 419385 반응식
[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C@@H:6]([C:15]([OH:17])=O)[CH2:5][O:4][CH2:3]1.ON1C2C=CC=CC=2N=N1.CN1CCOCC1.[CH2:35]([NH2:42])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl>[O:1]=[C:2]1[N:7]([CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C@@H:6]([C:15]([NH:42][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:17])[CH2:5][O:4][CH2:3]1

참가 물질

7

반응물 5

HCID 7504BenzylamineHCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 13543371(R)-4-Benzyl-5-oxo-3-morpholinecarboxylic Acid

생성물 1

HCID 59452664(3R)-5-oxo-N,4-bis(phenylmethyl)-3-morpholinecarboxamide수율 100%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

(3R)-5-oxo-4-(phenylmethyl)-3-morpholinecarboxylic acid (3.67 g, 15.6 mmol) and 1-hydroxybenzotriazole (2.53 g, 18.7 mmol) in DCM (50 mL) cooled to 0° C. N-Methylmorpholine (8.50 mL, 77.3 mmol), benzylamine (1.87 mL, 17.2 mmol) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (3.26 g, 17.2 mmol) added sequentially. The reaction was stirred at rt overnight, washed with H2O (50 mL), 6N HCl (30 mL), H2O (50 mL) and dried over MgSO4 to provide the title compound of step C (5.09 g, 15.6 mmol, 100%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.59 (d, J=15.2 Hz, 1H), 3.82 (t, J=2.9 Hz, 1H), 3.86-3.97 (m, 2H), 4.07-4.17 (m, 2H), 4.23-4.34 (m, 2H), 5.30 (d, J=15.4 Hz, 1H), 7.17-7.22 (m, 5H), 7.24-7.32 (m, 5H), 8.60 (t, J=5.6 Hz, 1H).

후처리

  1. washwashed with H2O (50 mL), 6N HCl (30 mL), H2O (50 mL)
  2. dry with materialdried over MgSO4

출처 및 근거

ORD 기록
ord-ff0507a7b19f431ba85fd0cfdd1636b1
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08093239B2

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