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Citric Acid → (S)-4-(1-hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzylester 1-tert-butyl ester

HRID 604977
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HRID 604977 반응식
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:11]([O:15][C:16]([N:18]1[C:22](=[O:23])[CH2:21][CH2:20][C@H:19]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:17])([CH3:14])([CH3:13])[CH3:12].B(F)(F)F.CCOCC.C(O)(=O)[CH2:44][C:45](CC(O)=O)([C:47](O)=O)[OH:46]>O1CCCC1.CC(C)=O>[C:11]([O:15][C:16]([N:18]1[C:22](=[O:23])[CH:21]([C:45]([OH:46])([CH3:47])[CH3:44])[CH2:20][C@H:19]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25])=[O:17])([CH3:14])([CH3:12])[CH3:13]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 311Citric AcidHCID 8000Boron trifluoride etherateHCID 2733832Lithium HexamethyldisilazideHCID 80274822-Benzyl 1-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate

생성물 1

HCID 58298416(S)-4-(1-hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzylester 1-tert-butyl ester

시약·촉매·용매 2

HCID 180
Acetone
용매
HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of lithium hexamethyldisilazide in tetrahydrofuran is cooled to −78° C. and treated with a solution of 15.95 g of (S)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzyl ester 1-tert-butyl ester in 100 mL of tetrahydrofuran maintaining the temperature at −78° C. The resulting mixture was stirred for 40 minutes and a mixture of 40 mL of acetone and 7 mL of boron trifluoride diethyl etherate added within 20 minutes. The reaction mixture is stirred for 2.5 hours at −78° C. and 300 mL of a 10% solution of citric acid added and the reaction mixture warmed to room temperature. The layers are separated and the aqueous layer is re-extracted with 300 mL of dichloromethane. The combined organic layers are dried, filtered and the solvent removed to give (S)-4-(1-hydroxy-1-methyl-ethyl)-5-oxo-pyrrolidine-1,2-dicarboxylic acid 2-benzylester 1-tert-butyl ester as an oil.

후처리

  1. additionadded within 20 minutes
  2. stirringThe reaction mixture is stirred for 2.5 hours at −78° C.
  3. customThe layers are separated
  4. extractionthe aqueous layer is re-extracted with 300 mL of dichloromethane
  5. customThe combined organic layers are dried
  6. filtrationfiltered
  7. customthe solvent removed

출처 및 근거

ORD 기록
ord-51153973a160419aa74d850b7d8afc5f
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07910774B2

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