Dicyclohexylcarbodiimide → 1-[2-(Benzyloxycarbonylamino)acetyl]-2,2-dimethyl-4-imidazolidinone

HRID 256353Notes

Reaction equation

HRID 256353 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.[CH3:16][C:17]1([CH3:23])[NH:21][C:20](=[O:22])[CH2:19][NH:18]1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([N:18]1[CH2:19][C:20](=[O:22])[NH:21][C:17]1([CH3:23])[CH3:16])=[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 212792952,2-Dimethylimidazolidin-4-one

Product 1

HCID 201637311-[2-(Benzyloxycarbonylamino)acetyl]-2,2-dimethyl-4-imidazolidinone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
20 °C

Procedure

To an ice-cold solution of N-(benzyloxycarbonyl) glycine (9 g) and 2,2-dimethyl-4-imidazolidinone (5 g) in tetrahydrofuran (THF) (150 ml) a solution of dicyclohexylcarbodiimide (DCC) (9 g) in THF (50 ml) was added dropwise. After stirring for 3 hours at 20° C., the precipitate was filtered off, the filtrate was evaporated to dryness and the residue was crystallized from 2-propanol affording 12 g of the title compound, m.p. 135°-136° C.

Workup

  1. filtrationthe precipitate was filtered off
  2. customthe filtrate was evaporated to dryness
  3. customthe residue was crystallized from 2-propanol affording 12 g of the title compound, m.p. 135°-136° C.

Sources & evidence

ORD record
ord-cc6c00ac38d44d00a5d397f316c069a1
Source dataset
uspto-grants-1987_10
Patent number
US04703054

Reaction notes

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