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Sodium triacetoxyborohydride → N-[2-Oxo-2-({(3R)-1-[4-(1,3-thiazol-2-yl)cyclohexyl]pyrrolidin-3-yl}amino)ethyl]-3-(trifluoromethyl)benzamide

HRID 1016043
ノート
印刷プレビュー

反応式

HRID 1016043 の反応式
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH:6]1[CH2:11][CH2:10][C:9](=O)[CH2:8][CH2:7]1.[O:13]=[C:14]([NH:29][CH2:30][C:31](=O)[NH:32][C@@H:33]1[CH2:37]CNC1)[CH2:15][NH:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>CC(O)=O.C(Cl)Cl.CCOC(C)=O>[O:13]=[C:14]([NH:29][C@@H:30]1[CH2:37][CH2:33][N:32]([CH:9]2[CH2:10][CH2:11][CH:6]([C:2]3[S:1][CH:5]=[CH:4][N:3]=3)[CH2:7][CH2:8]2)[CH2:31]1)[CH2:15][NH:16][C:17](=[O:28])[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 5049666Sodium triacetoxyborohydrideHCID 595561194-(Thiazol-2-yl)cyclohexan-1-oneHCID 66787189N-[2-oxo-2-({2-oxo-2-[(3R)-pyrrolidin-3-ylamino]ethyl}amino)ethyl]-3-(trifluoromethyl)benzamide

生成物 1

HCID 58751589N-[2-Oxo-2-({(3R)-1-[4-(1,3-thiazol-2-yl)cyclohexyl]pyrrolidin-3-yl}amino)ethyl]-3-(trifluoromethyl)benzamide収率 85%

試薬・触媒・溶媒 2

HCID 8857
Ethyl Acetate
溶媒
HCID 21922555Acetic acid methylene chloride溶媒

実験手順

To a mixture of 4-(1,3-thiazol-2-yl)cyclohexanone (0.069 g, 0.38 mmol) and N-[2-oxo-2-({2-oxo-2-[(3R)-pyrrolidin-3-ylamino]ethyl}amino)ethyl]-3-(trifluoromethyl)benzamide (0.10 g, 0.32 mmol) in 2% AcOH/CH2Cl2 (10 mL) was added NaB(OAc)3H (0.134 g, 0.634 mmol). After being stirred overnight at room temperature under N2, the reaction mixture was diluted with EtOAc and washed with saturated Na2CO3. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried (MgSO4), concentrated and flash chromatographed [EtOAc to MeOH/EtOAc (1:9) then to 5% MeOH/EtOAc/Et3N (1:9:0.5)] to give 0.129 g of the title compound in 85% yield. MS (EI) calcd: (M+H)+=480.2; found: 480.3.

後処理

  1. washwashed with saturated Na2CO3
  2. extractionThe aqueous layer was extracted with EtOAc (3×)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. concentrationconcentrated
  5. customflash chromatographed [EtOAc to MeOH/EtOAc (1:9)

出典と根拠

ORDレコード
ord-f09fba1193d04754a2cb2c86af4e6661
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07985730B2

反応ノート

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