1,2-Dichloroethane → (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetamide

HRID 2201059

반응식

HRID 2201059 반응식
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12](O)=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].C1C=C2[N:27]=NN(O)C2=CC=1.O.C(Cl)CCl.[NH4+].[OH-]>CN(C=O)C.CCOC(C)=O.O>[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C@H:11]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:12]([NH2:27])=[O:13])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]

참가 물질

8

반응물 4

HCID 111,2-DichloroethaneHCID 14923Ammonium HydroxideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67509737(R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetic acid

생성물 1

HCID 67508351(R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetamide수율 87.5%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetic acid (90 mg, 0.27 mmol) and HOBt hydrate (62 mg, 0.40 mmol) in DMF (2 mL), EDC (74 mg, 0.38 mmol) was added. The mixture was stirred for 60 min. Then conc. NH4OH (0.100 mL, ˜1.40 mmol) was added. It was stirred for 18 h. Water and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give (R)-2-(3-bromo-4-cyanophenylamino)-2-phenylacetamide (78 mg).

후처리

  1. stirringIt was stirred for 18 h
  2. customThe organic phase was separated
  3. washwashed with 5% NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-c375bb37bce748f28dca743fb23e9aaa
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359375B2

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