Benzyl chloroformate → Benzyloxycarbonyl-L-proline

HRID 654458Notes

Reaction equation

HRID 654458 reaction equation
[NH:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4].Cl[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]>[OH-].[Na+]>[CH2:13]([O:12][C:10]([N:1]1[CH2:8][CH2:7][CH2:6][C@H:2]1[C:3]([OH:5])=[O:4])=[O:11])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 2

HCID 10387Benzyl chloroformateHCID 145742L-Proline

Product 1

HCID 101987Benzyloxycarbonyl-L-proline

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent2×

Procedure

L-Proline 5 (100 gms, 0.87 moles) was dissolved in 2N sodium hydroxide (430 mL) and cooled in an ice bath. A further 220 mL of 4N sodium hydroxide was added simultaneously with benzyl chloroformate (155 gms, 0.90 moles) over 2 hrs. The reaction was then allowed to warm to room temperature overnight.

Workup

  1. temperaturecooled in an ice bath

Sources & evidence

ORD record
ord-557a042b66d6477799d1957c0f9f8ad4
Source dataset
uspto-grants-1992_07
Patent number
US05132301

Reaction notes

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