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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
ノート
印刷プレビュー

反応式

HRID 529484 の反応式
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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-c46ac038bc664915900f0838e807ddd1
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09346852B2

反応ノート

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