Sodium Bicarbonate → Sitagliptin

HRID 445966

反応式

HRID 445966 の反応式
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]

参加物

7

反応物 3

HCID 516892Sodium BicarbonateHCID 113066913-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-oneHCID 122598382Dibezoyl-D-tartaric acid monohydrate

生成物 3

HCID 4369359SitagliptinHCID 113066913-Amino-1-(3-(trifluoromethyl)-5,6-dihydro(1,2,4)triazolo(4,3-a)pyrazin-7(8H)-yl)-4-(2,4,5-trifluorophenyl)butan-1-oneHCID 12362977Di-benzoyl-d-tartaric acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

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%).

後処理

  1. filtrationThe salt was filtered off
  2. customfiltrate was collected
  3. distillationSolvent was distilled out from the filtrate
  4. customto obtain enantiomerically
  5. distillationSolvent was again distilled out
  6. dissolutionThe residue was dissolved in ethyl acetate
  7. washwashed with water and brine solution
  8. extractionEthyl acetate extract
  9. customwas collected
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationEthyl acetate was distilled out

出典と根拠

ORDレコード
ord-05add0ed16d84102bf657b6d57ef3112
出典データセット
uspto-grants-2013_07
特許番号
US08476437B2

関連ノート

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