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

HRID 419385ノート

反応式

HRID 419385 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-ff0507a7b19f431ba85fd0cfdd1636b1
出典データセット
uspto-grants-2012_01
特許番号
US08093239B2

反応ノート

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