Sodium Hydroxide → Tert-butyl[1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate

HRID 492910노트

반응식

HRID 492910 반응식
Cl.CN(C(C)C(O)=[O:7])C.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=N[CH2:26][CH2:27][CH2:28][N:29]([CH3:31])[CH3:30])C.[C:32]([O:36][C:37]([NH:39][CH:40]1[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]1)=[O:38])([CH3:35])([CH3:34])[CH3:33].[OH-].[Na+]>CN(C)C=O.[Cl-].[Na+].O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:30][N:29]([CH3:31])[CH2:28][CH2:27][C:26]([N:43]1[CH2:42][CH2:41][CH:40]([NH:39][C:37](=[O:38])[O:36][C:32]([CH3:35])([CH3:33])[CH3:34])[CH2:45][CH2:44]1)=[O:7]

참가 물질

10

반응물 5

HCID 14798Sodium HydroxideHCID 757711-HydroxybenzotriazoleHCID 7238334-(N-Boc-amino)piperidineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 216146742-Dimethylamino-propionic acid hydrochloride

생성물 1

HCID 57677405Tert-butyl[1-(3-dimethylaminopropionyl)piperidin-4-yl]carbamate수율 104.2%

시약·촉매·용매 4

HCID 6228Dimethylformamide용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

After adding N,N-dimethylaminopropionic acid hydrochloride (1.46 g), triethylamine (1.45 ml), 1-hydroxybenzotriazole (1.93 g) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.19 g) to a solution of 4-(tert-butoxycarbonylamino)piperidine (1.9 g) in N,N-dimethylformamide (30 ml), the mixture was stirred for 27.5 hours at room temperature under a nitrogen atmosphere. Ethyl acetate (200 ml), brine (50 ml) and 1N aqueous sodium hydroxide (50 ml) were added to the reaction mixture and stirred therewith at room temperature for 30 minutes, and then the mixture was partitioned. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, and then washed with 1N aqueous sodium hydroxide and brine and dried over anhydrous sodium sulfate. The dried organic layer was concentrated under reduced pressure to provide the title compound (2.96 g, quantitative) as pale yellow crystals.

후처리

  1. stirringstirred
  2. waitat room temperature for 30 minutes
  3. customthe mixture was partitioned
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washwashed with 1N aqueous sodium hydroxide and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationThe dried organic layer was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-e51d5ec59e544627914ced4de06827d2
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07531532B2

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