HRID445966

反应详情

EQUATION

反应方程式

REACTANTS

反应物

HCID516892

Sodium Bicarbonate

CHNaO3

结构：NC(CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F

HCID11306691

未命名化合物

结构：O.O=C(O)[C@](O)(C(=O)c1ccccc1)[C@](O)(C(=O)O)C(=O)c1ccccc1

HCID122598382

未命名化合物

PRODUCTS

生成物

结构：N[C@@H](CC(=O)N1CCn2c(nnc2C(F)(F)F)C1)Cc1cc(F)c(F)cc1F

HCID4369359

Sitagliptin

C16H15F6N5O

HCID11306691

未命名化合物

结构：O=C(O)[C@](O)(C(=O)c1ccccc1)[C@](O)(C(=O)O)C(=O)c1ccccc1

HCID12362977

未命名化合物

AUXILIARIES

试剂、催化剂与溶剂

溶剂HCID887

Methanol

CH4O

2 次

PROCEDURE

实验过程

Dibenzoyl-D-tartaric acid salt of 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine was prepared by reacting Dibezoyl-D-tartaric acid monohydrate and 4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine in molar equivalent ratio in methanol. The salt was filtered off and filtrate was collected. Solvent was distilled out from the filtrate to obtain enantiomerically enriched desired isomer which was basified in aq. methanol by using NaHCO3. Solvent was again distilled out. The residue was dissolved in ethyl acetate and washed with water and brine solution. Ethyl acetate extract was collected and dried over anhydrous sodium sulfate. Ethyl acetate was distilled out to obtain (2R)-4-oxo-4-[3-(trifluoromethyl)-5,6-dihydro[1,2,4]triazolo[4,3-a]pyrazin-7(8H)-yl]-1-(2,4,5-trifluorophenyl)butan-2-amine (% Purity by HPLC-88%, % Chiral purity by HPLC-90.0%).

WORKUP

后处理

filtrationThe salt was filtered off
customfiltrate was collected
distillationSolvent was distilled out from the filtrate
customto obtain enantiomerically
distillationSolvent was again distilled out
dissolutionThe residue was dissolved in ethyl acetate
washwashed with water and brine solution
extractionEthyl acetate extract
customwas collected
dry with materialdried over anhydrous sodium sulfate
distillationEthyl acetate was distilled out

来源与证据

来源类型: Open Reaction Database
ORD 记录: ord-05add0ed16d84102bf657b6d57ef3112
来源数据集: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
专利: US08476437B2
来源说明: uspto-grants-2013_07

反应 SMILES

O.[C:2]([C@:10]([C:25]([OH:27])=[O:26])([OH:24])[C@:11]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:15])[C:12]([OH:14])=[O:13])(=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].C([O-])(O)=O.[Na+]>CO>[C:16]([C@:11]([C:12]([OH:14])=[O:13])([OH:15])[C@:10]([C:2](=[O:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1)([OH:24])[C:25]([OH:27])=[O:26])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][CH:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41].[O:28]=[C:29]([N:43]1[CH2:48][CH2:47][N:46]2[C:49]([C:52]([F:55])([F:54])[F:53])=[N:50][N:51]=[C:45]2[CH2:44]1)[CH2:30][C@H:31]([NH2:42])[CH2:32][C:33]1[CH:38]=[C:37]([F:39])[C:36]([F:40])=[CH:35][C:34]=1[F:41]