Dimethylcarbamoyl Chloride → HCID 131711849, compound

HRID 1856003Notes

Reaction equation

HRID 1856003 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-4ba498f962804c95bfc917e405c5964b
Source dataset
uspto-grants-1980_08
Patent number
US04217359

Reaction notes

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