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Trifluoroacetic acid → (4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile

HRID 529486
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HRID 529486 반응식
FC(F)(F)C(O)=O.[C:8]([C@H:10]1[N:20]2[C@@H:14]([S:15][CH2:16][CH2:17][C@H:18]([NH:22]C(=O)OC(C)(C)C)[C:19]2=[O:21])[CH2:13][CH2:12][CH2:11]1)#[N:9]>C(Cl)Cl>[NH2:22][C@H:18]1[CH2:17][CH2:16][S:15][C@H:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([C:8]#[N:9])[N:20]2[C:19]1=[O:21]
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참가 물질

4

반응물 2

HCID 6422Trifluoroacetic acidHCID 86706201tert-butyl (4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

생성물 1

HCID 68292315(4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile수율 60.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Trifluoroacetic acid (0.15 mL) was added to a 0° C. solution of tert-butyl (4S,7S,10aS)-7-cyano-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (36 mg, 0.11 mmol) in DCM (0.35 mL). The reaction mixture was then stirred at rt for 45 min. The reaction mixture was concentrated. The residue was partitioned between EtOAc and saturated aqueous NaHCO3. The EtOAc was isolated, dried over MgSO4, filtered and concentrated give (4S,7S,10aS)-4-amino-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carbonitrile (15 mg, 0.067 mmol, 60% yield).

후처리

  1. concentrationThe reaction mixture was concentrated
  2. customThe residue was partitioned between EtOAc and saturated aqueous NaHCO3
  3. customThe EtOAc was isolated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-eb5a4c40e1c947288cf3ae3deabd9079
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346852B2

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