Potassium Carbonate → (2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol

HRID 2383074노트

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HRID 2383074 반응식
Cl[CH2:2][C:3]([N:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:4].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:28][C@@H:29]([CH2:32][CH:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1)[CH2:30][OH:31].[Cl-].[NH4+]>C(#N)C>[CH:33]1([CH2:32][C@H:29]([NH:28][CH2:2][C:3]([N:5]2[CH2:14][CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]2[CH:15]2[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]2)=[O:4])[CH2:30][OH:31])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

참가 물질

6

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 16212813(2S)-2-amino-3-cyclohexylpropan-1-ol hydrochlorideHCID 675372192-(Chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline

생성물 1

HCID 59396522(2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol수율 24.2%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

To a solution of 2-(chloroacetyl)-1-cyclohexyl-1,2,3,4-tetrahydroisoquinoline (12 mg) in acetonitrile (0.5 mL) were added potassium carbonate (3 mg) and (S)-(+)-2-amino-3-cyclohexyl-1-propanol hydrochloride (15 mg), followed by stirring at 80° C. for 4 hours. Thereafter, a saturated aqueous ammonium chloride solution was added to the reaction liquid, followed by extraction with chloroform. The solvent was evaporated and the resulting residue was purified by preparative HPLC to obtain (2S)-3-cyclohexyl-2-{[2-(1-cyclohexyl-3,4-dihydroisoquinolin-2(1H)-yl)-2-oxoethyl]amino}propan-1-ol (4.1 mg).

후처리

  1. extractionfollowed by extraction with chloroform
  2. customThe solvent was evaporated
  3. customthe resulting residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-310254a4ff5a409fafc0cbb4379920d4
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263607B2

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