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4-Methylmorpholine → tert-butyl (4S,7S,10aS)-7-carbamoyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate

HRID 529484
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HRID 529484 반응식
ClC(OCC(C)C)=O.[C:9]([O:13][C:14]([NH:16][C@H:17]1[CH2:23][CH2:22][S:21][C@H:20]2[CH2:24][CH2:25][CH2:26][C@@H:27]([C:28]([OH:30])=O)[N:19]2[C:18]1=[O:31])=[O:15])([CH3:12])([CH3:11])[CH3:10].C[N:33]1CCOCC1.[NH4+].[OH-]>C(Cl)Cl>[C:28]([C@H:27]1[N:19]2[C@@H:20]([S:21][CH2:22][CH2:23][C@H:17]([NH:16][C:14](=[O:15])[O:13][C:9]([CH3:11])([CH3:10])[CH3:12])[C:18]2=[O:31])[CH2:24][CH2:25][CH2:26]1)(=[O:30])[NH2:33]
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참가 물질

6

반응물 4

HCID 79724-MethylmorpholineHCID 14923Ammonium HydroxideHCID 62365Isobutyl chloroformateHCID 68292173(4S,7S,10aS)-4-(tert-butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid

생성물 1

HCID 68311221tert-butyl (4S,7S,10aS)-7-carbamoyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate수율 90.9%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

Isobutyl chloroformate (31.2 mg, 0.229 mmol) was added to a solution of (4S,7S,10aS)-4-(tert-Butoxycarbonylamino)-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepine-7-carboxylic acid (75 mg, 0.22 mmol) and 4-methylmorpholine (26.4 mg, 0.261 mmol) in DCM at 0° C. After stirring for 30 min at 0° C., NH4OH was added. The ice bath was removed and the reaction mixture was stirred at rt for 30 min. The reaction mixture was concentrated and the residue was partitioned between EtOAc and aqueous 0.5 N HCl. The organic phase was isolated, washed with saturated aqueous NaHCO3 and saturated aqueous NaCl, dried over MgSO4, filtered and concentrated to give tert-butyl (4S,7S,10aS)-7-carbamoyl-5-oxooctahydro-2H-pyrido[2,1-b][1,3]thiazepin-4-ylcarbamate (67 mg, 0.20 mmol, 90% yield) as an oil. Anal. Calcd. for C15H25N3O4S m/z 343.4. found: 344.3 (M+H)+.

후처리

  1. customThe ice bath was removed
  2. stirringthe reaction mixture was stirred at rt for 30 min
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was partitioned between EtOAc and aqueous 0.5 N HCl
  5. customThe organic phase was isolated
  6. washwashed with saturated aqueous NaHCO3 and saturated aqueous NaCl
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-c46ac038bc664915900f0838e807ddd1
출처 데이터셋
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09346852B2

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