Diazomethane → HCID 13942746, compound

HRID 1733344Notes

Reaction equation

HRID 1733344 reaction equation
[C:1]([N:11]1[CH2:18][CH:17]([OH:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[N+](=[CH2:22])=[N-]>O1CCOCC1>[C:1]([N:11]1[CH2:18][CH:17]([OH:19])[CH2:16][C@H:12]1[C:13]([O:15][CH3:22])=[O:14])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 12731799(2S)-1-((benzyloxy)carbonyl)-4-hydroxypyrrolidine-2-carboxylic acid

Product 1

HCID 13942746HCID 13942746, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Carbobenzyloxy-4-hydroxy-L-proline [12.4 g. (0.047 mole)] is esterified with diazomethane in dioxane-ether as described in JACS, 79, 191 (1957). To avoid freezing of the dioxane the addition of the diazomethane solution is begun at 10° and completed at 0°-2°. The yield of nearly colorless viscous oil is 14.6 g. (100%).

Workup

  1. customis begun at 10°
  2. customcompleted at 0°-2°

Sources & evidence

ORD record
ord-b663519934ee4212a3b57e09f4d71135
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

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