Ethyl chloroformate → (S)-tert-Butyl 2-((3-(3,4-dimethoxyphenoxy)-2-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate

HRID 710063노트

반응식

HRID 710063 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]([OH:15])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClC(OCC)=O.Cl.[NH2:23][CH2:24][C:25](=[O:38])[CH2:26][O:27][C:28]1[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[C:30]([O:36][CH3:37])[CH:29]=1>O.C1COCC1.CCN(CC)CC>[CH3:37][O:36][C:30]1[CH:29]=[C:28]([CH:33]=[CH:32][C:31]=1[O:34][CH3:35])[O:27][CH2:26][C:25](=[O:38])[CH2:24][NH:23][C:13]([C@@H:9]1[CH2:10][CH2:11][CH2:12][N:8]1[C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])=[O:15]

참가 물질

7

반응물 3

HCID 10928Ethyl chloroformateHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-HCID 867067751-Amino-3-(3,4-dimethoxyphenoxy)propan-2-one hydrochloride

생성물 1

HCID 86706777(S)-tert-Butyl 2-((3-(3,4-dimethoxyphenoxy)-2-oxopropyl)carbamoyl)pyrrolidine-1-carboxylate수율 49.4%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8471Triethylamine용매

실험 절차

To a THF (14 ml) solution of (S)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid (0.557 g) and Et3N (0.790 ml), ethyl chloroformate (0.295 g) was added over an ice bath, followed by stirring at the same temperature for 30 minutes. The reaction mixture was added at 0° C. to a THF (7 ml) solution of the compound (0.701 g) obtained in Example 19-(3) and the mixture was stirred at room temperature for 17 hours. After adding water and performing extraction with AcOEt, the organic layer was washed with saturated aqueous sodium chloride, dried (MgSO4), filtered and concentrated to give a crude product, which was further purified by silica gel chromatography (AcOEt/hexane) to give the titled compound (0.540 g, brown amorphous.)

후처리

  1. stirringthe mixture was stirred at room temperature for 17 hours
  2. extractionextraction with AcOEt
  3. washthe organic layer was washed with saturated aqueous sodium chloride
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas further purified by silica gel chromatography (AcOEt/hexane)

출처 및 근거

ORD 기록
ord-b5816afde8eb491888adea536c4c062a
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09181229B2

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