1,2-Dimethoxyethane → N-((1,1-Dimethylethoxy)carbonyl)-L-valyl-L-proline methyl ester

HRID 1461683Notes

Reaction equation

HRID 1461683 reaction equation
C([N:3]([CH2:6][CH3:7])[CH2:4][CH3:5])C.P(C#N)(=O)([O:12][CH2:13]C)OCC.[CH3:18][CH:19]([C@H:21]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:22]([OH:24])=O)[CH3:20].[CH3:33][O:34]CCOC>C(OCC)(=O)C>[NH:25]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C@H:21]([C:22]([N:3]1[CH2:4][CH2:5][CH2:7][C@H:6]1[C:33]([O:12][CH3:13])=[O:34])=[O:24])[CH:19]([CH3:18])[CH3:20]

Participants

6

Reactant 4

HCID 80711,2-DimethoxyethaneHCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 83693Boc-L-Valine

Product 1

HCID 11416197N-((1,1-Dimethylethoxy)carbonyl)-L-valyl-L-proline methyl ester

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

In one practice of the present invention, triethylamine and diethyl phosphorocyanidate ("DEPC") are added to S-proline methyl ester and N-t-Boc-L-valine in 1,2-dimethoxyethane at 0° C. After holding for one hour at 0° C., the mixture is allowed to warm to room temperature ("RT") over 4 hours and diluted with ethyl acetate. The diluted mixture is then washed with 5% HCl followed by sodium hydrogen carbonate followed with saturated brine. The solvent is then removed by vacuum (in vacuo) to yield N-t-Boc-L-Val-L-Pro-OMe as a colorless syrup.

Workup

  1. washThe diluted mixture is then washed with 5% HCl
  2. customThe solvent is then removed by vacuum (in vacuo)

Sources & evidence

ORD record
ord-5d573c2f42904fa48592e4e2e7f17122
Source dataset
uspto-grants-1991_12
Patent number
US05076973

Reaction notes

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