Dicyclohexylcarbodiimide → 3-Benzyloxy-1-(succinimidooxycarbonylmethyl)-pyrid-2-one

HRID 1906175Notes

Reaction equation

HRID 1906175 reaction equation
[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH2:15][C:16]([OH:18])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:21]1[C:25](=[O:26])[CH2:24][CH2:23][C:22]1=[O:27].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:10](=[O:19])[N:11]([CH2:15][C:16]([O:18][N:21]2[C:25](=[O:26])[CH2:24][CH2:23][C:22]2=[O:27])=[O:17])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 133367273-Benzyloxy-1-carboxymethylpyrid2-one

Product 1

HCID 133367283-Benzyloxy-1-(succinimidooxycarbonylmethyl)-pyrid-2-oneYield 82.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

3-Benzyloxy-1-carboxymethylpyrid-2-one (2 g) is dissolved in dimethylformamide (DMF) (25 ml) and to this solution is added N-hydroxysuccinimide (1 g). The resultant solution is cooled and to it is added dicyclohexylcarbodiimide (DCCI) (11.8 g) in DMF (5 ml). The mixture is allowed to stand overnight to give a brown supernatant and a white precipitate. The precipitate is filtered off, washed with a little DMF and then evaporated to dryness under high vacuum. The crude product is dissolved in a minimum volume of dichloromethane and diethyl ether is added to this solution until it becomes cloudy. The solution is then cooled and the resultant precipitate is filtered off and washed with a little diethyl ether to give 3-benzyloxy-1-(succinimidooxycarbonylmethyl)-pyrid-2-one (2.26 g, 82%), m.p. 187°-188° C.

Workup

  1. customto give a brown supernatant
  2. filtrationThe precipitate is filtered off
  3. washwashed with a little DMF
  4. customevaporated to dryness under high vacuum
  5. dissolutionThe crude product is dissolved in a minimum volume of dichloromethane and diethyl ether
  6. additionis added to this solution until it
  7. temperatureThe solution is then cooled
  8. filtrationthe resultant precipitate is filtered off
  9. washwashed with a little diethyl ether

Sources & evidence

ORD record
ord-688f039af8cf4918b2c5e5a7222ab992
Source dataset
uspto-grants-1987_03
Patent number
US04650793

Reaction notes

Loading…