Trifluoroacetic acid → (3S)-benzyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 2175828노트

반응식

HRID 2175828 반응식
[C:1]([C:3]1[C:4]([CH3:28])=[C:5]([CH:10]([OH:27])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20]C(C)(C)C)=[O:19])[CH2:14][C@H:13]2[CH2:25][OH:26])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2].FC(F)(F)C(O)=O.C(N(CC)CC)C.ClC(O[CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=O>C(Cl)Cl>[C:1]([C:3]1[C:4]([CH3:28])=[C:5]([CH:10]([OH:27])[CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][CH2:47][C:48]3[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=3)=[O:19])[CH2:14][C@H:13]2[CH2:25][OH:26])[CH:6]=[CH:7][C:8]=1[F:9])#[N:2]

참가 물질

6

반응물 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 71272768(3S)-tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

생성물 1

HCID 86727052(3S)-benzyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of (3S)-tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate (2.87 g, 7.32 mmol) in methylene chloride (20 mL) was added trifluoroacetic acid (20 mL) at rt, and the resulting solution was stirred at rt for 1 h. After removing the volatile solvents, the residue was dissolved in methylene chloride (50 mL). To the above solution was added triethylamine (6.12 mL, 43.9 mmol) and benzyl chloroformate (1.1 mL, 7.3 mmol) dropwise at 0° C. The reaction solution was stirred at 0° C. for 1 h before quenching with saturated sodium bicarbonate solution (200 mL). The mixture was then extracted with methylene chloride (3×100 mL). The combined organic phase was dried over sodium sulphate and concentrated to give the title compound. LC/MS: (M+1)+: 428.18.

후처리

  1. customAfter removing the volatile solvents
  2. dissolutionthe residue was dissolved in methylene chloride (50 mL)
  3. stirringThe reaction solution was stirred at 0° C. for 1 h
  4. custombefore quenching with saturated sodium bicarbonate solution (200 mL)
  5. extractionThe mixture was then extracted with methylene chloride (3×100 mL)
  6. dry with materialThe combined organic phase was dried over sodium sulphate
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-1a2147f5a0894957bab5f490be5ae120
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09062070B2

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