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4-Toluenesulfonyl chloride → N-tert-Butoxycarbonyl-cis-4-(p-Toluenesulfonyloxy)-D-Proline Methyl Ester

HRID 2185415
Notes
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Reaction equation

HRID 2185415 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[CH3:12][O:13][C:14](=[O:28])[C@H:15]1[CH2:19][C@@H:18]([OH:20])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22]>CN(C)C1C=CN=CC=1.ClCCl>[CH3:12][O:13][C:14](=[O:28])[C@H:15]1[CH2:19][C@@H:18]([O:20][S:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:11])=[CH:2][CH:3]=2)(=[O:9])=[O:8])[CH2:17][N:16]1[C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 6951202(2R,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 13425770N-tert-Butoxycarbonyl-cis-4-(p-Toluenesulfonyloxy)-D-Proline Methyl Ester

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344
Dichloromethane
Solvent

Procedure

4-Dimethylaminopyridine (1.21 g) and p-toluenesulfonyl chloride (1.51 g) were added to a solution of N-tert-butoxycarbonyl-cis-4-hydroxy-D-proline methyl ester (A, 971 mg) in dichloromethane (20 mL). After stirrng at room temperature for 4 hr, the solvent was removed in vacuo. The residue was diluted with ethyl acetate, and washed with 10% citric acid, water, and brine. The organic layer was dried over anhydrous sodium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (chloroform then chloroform:ethyl acetate=1:50, v/v) to give the title compound (1.65 g) as a colorless oil.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was diluted with ethyl acetate
  3. washwashed with 10% citric acid, water, and brine
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography (chloroform

Sources & evidence

ORD record
ord-69920ede65644d28adbf8517628fbcb8
Source dataset
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06399629B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes