Dicyclohexylcarbodiimide → HCID 47451380, compound

HRID 963420Notes

Reaction equation

HRID 963420 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:9]([NH:16][CH2:17][C:18](O)=[O:19])([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[I:1][C:2]1[CH:3]=[C:4]([NH:5][C:18]([CH2:17][NH:16][C:9](=[O:10])[O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 122713-IodoanilineHCID 78288N-(tert-butoxycarbonyl)glycine

Product 1

HCID 47451380HCID 47451380, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.15 g of 3-iodoaniline and 097 g of N-BOC-glycine are dissolved in 25 ml of methylene chloride and treated portionwise at 0° with 1.14 g of dicyclohexylcarbodiimide. The separated urea is filtered off and the filtrate is concentrated. Recrystallization from toluene yields tert.butyl [(3-iodo-phenyl-carbamoyl)-methyl]-carbamate as colourless crystals. Yield: 60%. M.p.=126°-128°.

Workup

  1. filtrationThe separated urea is filtered off
  2. concentrationthe filtrate is concentrated
  3. customRecrystallization from toluene

Sources & evidence

ORD record
ord-a721d98f5e334642b0fe42ca3fa85208
Source dataset
uspto-grants-1998_06
Patent number
US05763450

Reaction notes

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