HRID422896

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID11117869

未命名化合物

HCID21864993

4-Nitrophenyl carbonate

C7H4NO5-

$结构：CCNC(=O)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@@H](O)CCc2ccccc2)[C@H](O)C[C@@H]1O.[O-]B[O-]$

HCID178465099

未命名化合物

PRODUCTS

生成物

$结构：CCNC(=O)CCC/C=C\C[C@@H]1[C@@H](/C=C/[C@H](CCc2ccccc2)OC(=O)OCCCC[C@@H](C)O[N+](=O)[O-])[C@H](O)C[C@@H]1O$

HCID58231638

未命名化合物

PROCEDURE

实验过程

Similar to Example R-1, except started Scheme R with antipodal tert-butyl (5R)-5-(acetoxy)hexanoate (Pamies, O.; Backvall, J.-E. J. Org. Chem. 2002, 67, 1261-1265) and eventually prepared antipode of crude p-nitrophenyl carbonate r-4, which was similarly used to acylate bimatoprost boronate (580 mg, 1.2 mmol) to provide after preparative HPLC purification, 420 mg (57%) of 15-acyl nitrate R-2.

WORKUP

后处理

customto provide
customafter preparative HPLC purification, 420 mg (57%) of 15-acyl nitrate R-2

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-7f1bfdd63ab448a0bfe89e4ebd211194
来源数据集: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08101658B2
来源说明: uspto-grants-2012_01

反应 SMILES

C([O:4][C@H:5]([CH3:16])[CH2:6][CH2:7][CH2:8][C:9]([O:11][C:12](C)(C)C)=O)(=O)C.C(=O)([O-])OC1C=CC([N+:25]([O-:27])=[O:26])=CC=1.[CH3:30][CH2:31][NH:32][C:33]([CH2:35][CH2:36][CH2:37]/[CH:38]=[CH:39]\[CH2:40][C@@H:41]1[C@@H:45](/[CH:46]=[CH:47]/[C@@H:48]([OH:57])[CH2:49][CH2:50][C:51]2[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=2)[C@H:44]([OH:58])[CH2:43][C@@H:42]1[OH:59])=[O:34].B([O-])[O-:61]>>[C:12](=[O:61])([O:11][CH2:9][CH2:8][CH2:7][CH2:6][C@H:5]([O:4][N+:25]([O-:27])=[O:26])[CH3:16])[O:57][C@@H:48]([CH2:49][CH2:50][C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1)/[CH:47]=[CH:46]/[C@H:45]1[C@H:44]([OH:58])[CH2:43][C@H:42]([OH:59])[C@@H:41]1[CH2:40]/[CH:39]=[CH:38]\[CH2:37][CH2:36][CH2:35][C:33]([NH:32][CH2:31][CH3:30])=[O:34]