Dicyclohexylcarbodiimide → HCID 20163732, compound

HRID 256354Notes

Reaction equation

HRID 256354 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]([CH:19]1[NH:23][C:22](=[O:24])[CH2:21][NH:20]1)([CH3:18])[CH3:17].C1CCC(N=C=NC2CCCCC2)CC1>C1COCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([N:20]1[CH2:21][C:22](=[O:24])[NH:23][CH:19]1[CH:16]([CH3:18])[CH3:17])=[O:15])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 14349BenzyloxycarbonylglycineHCID 13125043HCID 13125043, compound

Product 1

HCID 20163732HCID 20163732, compoundYield 84.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

Into an ice-cold solution of N-(benzyloxycarbonyl) glycine (26 g) and 2-isopropyl-4-imidazolidinone (16 g) in THF (260 ml), a solution of DCC (25.4 g) in THF (100 ml) was added dropwise. After stirring for 2 hours at 20° C., the precipitate was filtered off and the filtrate was evaporated to dryness. Crystallization of the residue from 2-propanol yielded 33.5 g of the title compound, m.p. 137°-139° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customCrystallization of the residue from 2-propanol

Sources & evidence

ORD record
ord-429b533f73bd4b2a94e800c84004030e
Source dataset
uspto-grants-1987_10
Patent number
US04703054

Reaction notes

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