Hydrochloric Acid → HCID 54035577, compound

HRID 1760153Notes

Reaction equation

HRID 1760153 reaction equation
[CH2:1]([O:10][C:11](=[O:24])[C@@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1C(OC(C)(C)C)=O)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3].Cl>CCOC(C)=O>[CH2:1]([O:10][C:11](=[O:24])[C@@H:12]1[CH2:16][CH2:15][CH2:14][NH:13]1)[C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[O:3]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 823719HCID 823719, compound

Product 1

HCID 54035577HCID 54035577, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Boc-L-proline phenacyl ester (0.29 g, 0.87 mmol) was dissolved in EtOAc (25 mL) and a steady current of HCl was passed through the solution for approximately 40 min, when TLC analysis showed the deprotection to be complete. The solvent was evaporated to provide a white crystalline material. Recrystallization from petroleum ether gave clear crystals (0.19 g, 94%); FABMS 234.2 (M+H), 467.2 (2M+H); HRFABMS calcd for C13H16NO3 (M+H) 234.1130, found 234.1129.

Workup

  1. customThe solvent was evaporated
  2. customto provide a white crystalline material
  3. customRecrystallization from petroleum ether

Sources & evidence

ORD record
ord-73abc54875b54a4395a56614e4e2afd9
Source dataset
uspto-grants-2005_01
Patent number
US06841530B2

Reaction notes

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