Dimethylcarbamoyl Chloride → HCID 131711849, compound

HRID 1414073Notes

Reaction equation

HRID 1414073 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]1[CH2:8][C@@H:7]([OH:9])[CH2:6][N:5]1[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11].[CH3:21][N:22]([CH3:26])[C:23](Cl)=[O:24]>C(Cl)(Cl)Cl>[C:10]([N:5]1[CH2:6][C@H:7]([O:9][C:23]([N:22]([CH3:26])[CH3:21])=[O:24])[CH2:8][C@H:4]1[C:3]([O:2][CH3:1])=[O:20])([O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:11]

Participants

4

Reactant 2

HCID 6598Dimethylcarbamoyl ChlorideHCID 6884112-Methyl 1-(phenylmethyl) (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Product 1

HCID 131711849HCID 131711849, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of N-carbobenzyloxy-trans-4-hydroxy-L-proline methyl ester (Example 1, part b) in chloroform is treated dropwise with an equivalent quantity of dimethylcarbamyl chloride. The mixture is stirred for two hours, washed with water and the organic phase is dried over MgSO4. The solution is filtered and solvent evaporated to give trans-N-carbobenzyloxy-4-[[(dimethylamino)carbonyl]oxy]-L-proline, methyl ester.

Workup

  1. washwashed with water
  2. dry with materialthe organic phase is dried over MgSO4
  3. filtrationThe solution is filtered
  4. customsolvent evaporated

Sources & evidence

ORD record
ord-7160d0de22f3471f9738246874a929e9
Source dataset
uspto-grants-1981_02
Patent number
US04252943

Reaction notes

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