HRID987994

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID24648

Sulfuryl chloride

Cl2O2S

结构：CC(C)(C)OC(=O)N[C@@H](Cc1ccc2ccccc2c1)C(=O)O

HCID7020908

Boc-3-(2-naphthyl)-L-alanine

C18H21NO4

结构：CC(C)CN([C@H](CO)CCCCN)S(=O)(=O)c1ccc(F)c(N)c1

HCID67531641

未命名化合物

PRODUCTS

生成物

结构：CC(C)CN([C@H](CO)CCCCNC(=O)[C@H](Cc1ccc2ccccc2c1)NC(=O)OC(C)(C)C)S(=O)(=O)c1ccc(F)c(N)c1

HCID514012

未命名化合物

收率 38%

PROCEDURE

实验过程

The title compound was prepared from the crude amine mixture of (1S)-N-(5-amino-1-hydroxymethyl-pentyl)-N-isobutyl-3-amino-4-fluoro-benzenesulfonamide which is described earlier (example 53, step C, which was made from a batch of sulfonyl chloride containing the two regioisomers) and (2S)-2-tert-butoxycarbonylamino-3-naphthalen-2-yl-propionic acid using general procedure A. The crude residue was purified by semi-preparative HPLC in several batches of 80 mg using a gradient of 35 to 90% of acetonitrile over 30 min and a flow rate of 15 mL/min, retention time=23.9 min. All the pure fractions were combined to provide 460 mg (38% yield) of the title compound.

WORKUP

后处理

customThe crude residue was purified by semi-preparative HPLC in several batches of 80 mg
customover 30 min

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-e9c8ac507a784ab08f8db9ab89dcb2c8
来源数据集: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
专利: US06632816B1
来源说明: uspto-grants-2003_10

反应 SMILES

[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([CH2:21][CH:22]([CH3:24])[CH3:23])[S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH2:20])[CH:14]=1)(=[O:12])=[O:11])[CH2:7][OH:8].S(Cl)(Cl)(=O)=O.[C:30]([O:34][C:35]([NH:37][C@@H:38]([CH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)[C:39](O)=[O:40])=[O:36])([CH3:33])([CH3:32])[CH3:31]>>[C:30]([O:34][C:35](=[O:36])[NH:37][C@H:38]([C:39](=[O:40])[NH:1][CH2:2][CH2:3][CH2:4][CH2:5][C@H:6]([N:9]([S:10]([C:13]1[CH:18]=[CH:17][C:16]([F:19])=[C:15]([NH2:20])[CH:14]=1)(=[O:12])=[O:11])[CH2:21][CH:22]([CH3:24])[CH3:23])[CH2:7][OH:8])[CH2:42][C:43]1[CH:52]=[CH:51][C:50]2[C:45](=[CH:46][CH:47]=[CH:48][CH:49]=2)[CH:44]=1)([CH3:31])([CH3:33])[CH3:32]