HRID1264397

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID15908

1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide

C8H17N3

HCID75771

1-Hydroxybenzotriazole

C6H5N3O

HCID14461641

未命名化合物

结构：O=C(O)[C@@H]1C[C@@H](SC(c2ccccc2)(c2ccccc2)c2ccccc2)CN1S(=O)(=O)c1ccc2ccccc2c1

HCID69428772

未命名化合物

PRODUCTS

生成物

结构：CC(C)(C)OC(=O)CN(CCc1ccccc1)C(=O)[C@@H]1C[C@@H](SC(c2ccccc2)(c2ccccc2)c2ccccc2)CN1S(=O)(=O)c1ccc2ccccc2c1

HCID70001340

未命名化合物

收率 26.4%

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID8028

Tetrahydrofuran

C4H8O

PROCEDURE

实验过程

A solution of 800 mg (1.38 mmol) (2S,4R)-1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carboxylic acid and 390 mg (1.66 mmol) crude phenethylamino-acetic acid tert-butyl ester in 14 ml THF was cooled to 0° C. and treated with 318 mg (1.66 mmol) EDCI and 19 mg (0.14 mmol) HOBT. The reaction was warmed up to RT over night and partitioned between aqueous 10% KHSO4/ethyl acetate (3×). The organic phases were washed with aqueous saturated NaHCO3 solution and dried over Na2SO4. Purification by flash-chromatography on silicagel (Hexane/EtOAc 4:1 to 1:1) gave 290 mg (26%) (2S,4R)-{[1-(Naphthalene-2-sulfonyl)-4-tritylsulfanyl-pyrrolidine-2-carbonyl]-phenethyl-amino}-acetic acid tert-butyl ester, MS: 797 (MH+)

WORKUP

后处理

custompartitioned between aqueous 10% KHSO4/ethyl acetate (3×)
washThe organic phases were washed with aqueous saturated NaHCO3 solution
dry with materialdried over Na2SO4
customPurification by flash-chromatography on silicagel (Hexane/EtOAc 4:1 to 1:1)

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-8205d4fa74a64b63aa9a846444454dba
来源数据集: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06541638B2
来源说明: uspto-grants-2003_04

反应 SMILES

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([N:14]1[CH2:18][C@H:17]([S:19][C:20]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16][C@H:15]1[C:39](O)=[O:40])(=[O:13])=[O:12].[C:42]([O:46][C:47](=[O:58])[CH2:48][NH:49][CH2:50][CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)([CH3:45])([CH3:44])[CH3:43].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C1COCC1>[C:42]([O:46][C:47](=[O:58])[CH2:48][N:49]([C:39]([C@@H:15]1[CH2:16][C@@H:17]([S:19][C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH2:18][N:14]1[S:11]([C:2]1[CH:1]=[CH:10][C:5]2[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:3]=1)(=[O:12])=[O:13])=[O:40])[CH2:50][CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)([CH3:45])([CH3:43])[CH3:44]