HRID2304327

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID7972

4-Methylmorpholine

C5H11NO

结构：CN(C)C(On1nnc2ccccc21)=[N+](C)C.F[B-](F)(F)F

HCID2733207

O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate

C11H16BF4N5O

HCID2733413

Benzyl L-prolinate hydrochloride

C12H16ClNO2

结构：CCOC(=O)CN(C(=O)OC(C)(C)C)[C@H](Cc1ccc(OC)cc1)C(=O)O

HCID22958574

未命名化合物

PRODUCTS

生成物

结构：CCOC(=O)CN(C(=O)OC(C)(C)C)[C@H](Cc1ccc(OC)cc1)C(=O)N1CCC[C@H]1C(=O)OCc1ccccc1

HCID69780750

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID962

Water

H2O

溶剂HCID6228

N,N-Dimethylformamide

C3H7NO

PROCEDURE

实验过程

A mixture of (L)-proline benzyl ester hydrochloride (0.49 g), N-Ethoxycarbonylmethyl-N-tert.-butoxycarbonyl-2-(R)-amino-3-(4-methoxyphenyl)-propionic acid (0.760 g), N-methyl morpholine (0.93 mL) and 0.65 g of 2-(1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium tetra-fluoroborate (TBTU) in 10 mL of dry N,N-dimethyl formamide was stirred for 16 h at ambient temperature. The volatiles were pumped off and water was added followed by extraction with ethyl acetate and concentration of the organic layer., The remaining residue was purified by silica chromatography (isohexane/ethyl acetate 1/2). Yield: 0.99 g (86%); colorless oil; (+)-APCI-MS: 569 (MH+).

WORKUP

后处理

extractionfollowed by extraction with ethyl acetate and concentration of the organic layer
custom, The remaining residue was purified by silica chromatography (isohexane/ethyl acetate 1/2)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-4f820ddce7074dca9eac2f689aead969
来源数据集: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06432955B1
来源说明: uspto-grants-2002_08

反应 SMILES

Cl.[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH2:17]([O:19][C:20]([CH2:22][N:23]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C@H:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:25](O)=[O:26])=[O:21])[CH3:18].CN1CCOCC1.F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C)C=O.O>[CH2:17]([O:19][C:20](=[O:21])[CH2:22][N:23]([C@H:24]([CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1)[C:25]([N:12]1[CH2:13][CH2:14][CH2:15][C@H:11]1[C:10]([O:9][CH2:2][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1)=[O:16])=[O:26])[C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[CH3:18]