HRID20427

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID6367

Acetyl chloride

C2H3ClO

HCID81531

Diisopropylethylamine

C8H19N

结构：CC1(CO[C@H]2CN(C(=O)OC(C)(C)C)[C@@H](C(O)C(N)Cc3cccc(OCc4ccccc4)c3)CO2)CCCC1

HCID68564333

未命名化合物

PRODUCTS

生成物

结构：CC(=O)N[C@@H](Cc1cccc(OCc2ccccc2)c1)[C@H](O)[C@H]1CO[C@@H](OCC2(C)CCCC2)CN1C(=O)OC(C)(C)C

HCID68561840

未命名化合物

收率 25%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID6344

Dichloromethane

CH2Cl2

溶剂HCID8857

Ethyl acetate

C4H8O2

PROCEDURE

实验过程

Add acetyl chloride (0.13 mL, 1.82 mmol) to an ice cold solution of (2R,5R)-5-[2-amino-3-(3-benzyloxyphenyl)-1-hydroxypropyl]-2-(1-methylcyclopentylmethoxy)-morpholine-4-carboxylic acid tert-butyl ester (0.91 g, 1.652 mmol) and N,N-diisopropyl-ethylamine (0.58 mL, 3.30 mmol) in dichloromethane (20 mL). Stir 15 minutes and dilute with ethyl acetate and wash with 1 N hydrochloric acid, saturated aqueous sodium chloride, dry (magnesium sulfate) and purify (silica gel chromatography, elutin with dichloromethane/ethyl acetate) to give the desired compound (246 mg).

WORKUP

后处理

washwash with 1 N hydrochloric acid, saturated aqueous sodium chloride
dry with materialdry (magnesium sulfate)
custompurify (silica gel chromatography, elutin with dichloromethane/ethyl acetate)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-b60a1c936d55443c9e11999a26e58356
来源数据集: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
专利: US07745438B2
来源说明: uspto-grants-2010_06

反应 SMILES

[C:1](Cl)(=[O:3])[CH3:2].[C:5]([O:9][C:10]([N:12]1[C@@H:17]([CH:18]([OH:36])[CH:19]([NH2:35])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)[CH2:16][O:15][C@@H:14]([O:37][CH2:38][C:39]2([CH3:44])[CH2:43][CH2:42][CH2:41][CH2:40]2)[CH2:13]1)=[O:11])([CH3:8])([CH3:7])[CH3:6].C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)(=O)C>[C:5]([O:9][C:10]([N:12]1[C@@H:17]([C@@H:18]([OH:36])[C@@H:19]([NH:35][C:1](=[O:3])[CH3:2])[CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([O:27][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[CH:22]=2)[CH2:16][O:15][C@@H:14]([O:37][CH2:38][C:39]2([CH3:44])[CH2:40][CH2:41][CH2:42][CH2:43]2)[CH2:13]1)=[O:11])([CH3:8])([CH3:6])[CH3:7]