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

HRID 710063ノート

反応式

HRID 710063 の反応式
[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]

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒

実験手順

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.)

後処理

  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)

出典と根拠

ORDレコード
ord-b5816afde8eb491888adea536c4c062a
出典データセット
uspto-grants-2015_11
特許番号
US09181229B2

反応ノート

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