D-Proline → HCID 86621516, compound

HRID 500260Notes

Reaction equation

HRID 500260 reaction equation
[Cl:1]N1C(=O)CCC1=O.[C:9]([O:13][C:14](=[O:26])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH2:23][CH:24]=[O:25])[CH:17]=1)([CH3:12])([CH3:11])[CH3:10].N1CCC[C@@H]1C(O)=O>C(Cl)Cl>[C:9]([O:13][C:14](=[O:26])[NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([CH2:22][CH:23]([Cl:1])[CH:24]=[O:25])[CH:17]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 8988D-ProlineHCID 31398ChlorosuccinimideHCID 86023971HCID 86023971, compound

Product 1

HCID 86621516HCID 86621516, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Chlorosuccinimide (0.27 g, 0.0020 mol) was added to a mixture of tert-butyl[3-(3-oxopropyl)phenyl]carbamate (0.50 g, 0.0020 mol) and D-proline (0.05 g, 0.0004 mol) in methylene chloride (5 mL) at 0° C. The reaction mixture was stirred at RT for 2 h and concentrated. The residue was purified by chromatography on silica gel with 30% EtOAc in hexanes to afford the desired product (0.50 g, 88%). LCMS: (M+H)=209.9/211.9.

Workup

  1. concentrationconcentrated
  2. customThe residue was purified by chromatography on silica gel with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-ac403203fcd24bdb9fdf3fac2cb1b8ce
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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