Potassium Carbonate → tert-butyl (3R)-4-[2-(3-cyano-4-fluorophenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 1501981

반응식

HRID 1501981 반응식
Br[CH2:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]([F:13])=[C:9]([CH:12]=1)[C:10]#[N:11])=[O:4].[OH:14][CH2:15][C@@H:16]1[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:10]([C:9]1[CH:12]=[C:5]([C:3](=[O:4])[CH2:2][N:21]2[CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[CH2:17][C@@H:16]2[CH2:15][OH:14])[CH:6]=[CH:7][C:8]=1[F:13])#[N:11]

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 24820286tert-Butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 867270445-(2-Bromoacetyl)-2-fluorobenzonitrile

생성물 1

HCID 86727046tert-butyl (3R)-4-[2-(3-cyano-4-fluorophenyl)-2-oxoethyl]-3-(hydroxymethyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a solution of 5-(bromoacetyl)-2-fluorobenzonitrile (13.1 g, 0.054 mol) in DMF (160 mL) was added tert-butyl (3R)-3-(hydroxymethyl)piperazine-1-carboxylate (13.1 g, 0.065 mol) and K2CO3 (11.77 g, 0.075 mol), and the mixture was stirred at r.t for 3 h. The mixture was washed with water, and extracted with EtOAc. The organic layer was washed with brine dried over Na2SO4 and concentrated in vacuum to give the desired product, which can be used for next step without further purification.

후처리

  1. washThe mixture was washed with water
  2. extractionextracted with EtOAc
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuum

출처 및 근거

ORD 기록
ord-69a9d84be61744a492fc7ec38df3df64
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09206199B2

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