Benzyloxycarbonyl-L-proline → 2-(1,1-Dimethylethyl) 1-(phenylmethyl) (2S)-1,2-pyrrolidinedicarboxylate

HRID 65709Notes

Reaction equation

HRID 65709 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:18][CH2:17][CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>ClCCl.CC(=C)C.S(=O)(=O)(O)O>[C:2]([O:14][C:13](=[O:15])[C@@H:12]1[CH2:16][CH2:17][CH2:18][N:11]1[C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])([CH3:7])([CH3:3])[CH3:1]

Participants

5

Reactant 1

HCID 101987Benzyloxycarbonyl-L-proline

Product 1

HCID 70197992-(1,1-Dimethylethyl) 1-(phenylmethyl) (2S)-1,2-pyrrolidinedicarboxylate

Reagents, catalysts & solvents 3

HCID 1118Sulfuric AcidSolventHCID 6344DichloromethaneSolventHCID 8255IsobutyleneSolvent2×

Procedure

The benzyloxycarbonyl-L-proline thus obtained (180 g.) is dissolved in a mixture of dichloromethane (300 ml.), liquid isobutylene (800 ml.) and concentrated sulfuric acid (7.2 ml.). The solution is shaken in a pressure bottle for 72 hours. The pressure is released, the isobutylene is allowed to evaporate and the solution is washed with 5% sodium carbonate, water, dried over magnesium sulfate and concentrated to dryness in vacuo, to obtain benyloxycarbonyl-L-proline tert.butyl ester, yield 205 g.

Workup

  1. customto evaporate
  2. washthe solution is washed with 5% sodium carbonate, water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated to dryness in vacuo

Sources & evidence

ORD record
ord-f9ebc023c0c940a697d43746e730fb8c
Source dataset
uspto-grants-1978_12
Patent number
US04128653

Reaction notes

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