Dicyclohexylcarbodiimide → Z-Gly-OSu

HRID 358515Notes

Reaction equation

HRID 358515 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([O:15][N:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=[O:23])=[O:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 80170N-Hydroxysuccinimide

Product 1

HCID 76177Z-Gly-OSuYield 53%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

N-Benzyloxycarbonylglycine (10.9 g, 52.2 mmol) and N-hydroxysuccinimide (6.0 g, 52.2 mmol), were dissolved in dioxane (100 ml) and cooled in a cold water bath. N,N'-Dicyclohexylcarbodiimide (10.8 g, 52.2 mmol) was added and the mixture was stirred overnight. The white precipitate which formed was filtered, washed and air-dried (11.8 g, 100% of dicyclohexylurea). The filtrate was evaporated to dryness under reduced pressure, and the residual solid (16.2 g) was crystallized from ethyl acetate (50 ml) to give 8.4 g (53%) of crystalline N-(N-benzyloxycarbonylglycyloxy)succinimide, m.p. 110.5-112° C.

Workup

  1. temperaturecooled in a cold water bath
  2. customThe white precipitate which formed
  3. filtrationwas filtered
  4. washwashed
  5. dry with materialair-dried (11.8 g, 100% of dicyclohexylurea)
  6. customThe filtrate was evaporated to dryness under reduced pressure
  7. customthe residual solid (16.2 g) was crystallized from ethyl acetate (50 ml)

Sources & evidence

ORD record
ord-bb542cfda08e4213b85a5e38e7ef7001
Source dataset
uspto-grants-1984_08
Patent number
US04468513

Reaction notes

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