Water → HCID 823719, compound

HRID 1760152Notes

Reaction equation

HRID 1760152 reaction equation
[C:1]([N:8]1[CH2:15][CH2:14][CH2:13][C@H:9]1[C:10]([OH:12])=[O:11])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].C(N(CC)CC)C.[CH2:23](Br)[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].O>C(OCC)(=O)C.CCOCC>[CH2:23]([O:11][C:10](=[O:12])[C@@H:9]1[CH2:13][CH2:14][CH2:15][N:8]1[C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2])[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 8471TriethylamineHCID 850831,2-Pyrrolidinedicarboxylic acid, 1-(1,1-dimethylethyl) ester, (2S)-

Product 1

HCID 823719HCID 823719, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

Boc-proline (1.00 g, 4.65 mmol) was dissolved in ethyl acetate (29.4 mL), triethylamine (0.46 g, 0.63 mL) and phenacyl bromide (0.93 g, 4.68 mmol) were added and, within a few minutes, a precipitate formed. The mixture was stirred overnight, water and ether were added and the two layers separated. The organic layer was washed with 0.1N HCl, saturated sodium bicarbonate, and brine, then dried over MgSO4. Evaporation of the solvent provided the desired compound (1.27 g, 83%); FABMS 334.2 (M+H), 234.1 (M+2H-Boc), 667.3 (2M+H); HRFABMS calcd for C18H23NO5 (M+H) 334.1654, found 334.1665.

Workup

  1. customa precipitate formed
  2. customthe two layers separated
  3. washThe organic layer was washed with 0.1N HCl, saturated sodium bicarbonate, and brine
  4. dry with materialdried over MgSO4
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-4604e41924fd46b4a4ec3776867ee3b7
Source dataset
uspto-grants-2005_01
Patent number
US06841530B2

Reaction notes

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