Dicyclohexylcarbodiimide → HCID 70212454, compound

HRID 380183Notes

Reaction equation

HRID 380183 reaction equation
[C:1]([NH:8][CH2:9][C:10]([OH:12])=O)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[CH3:13][CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH2:15][NH2:16].[OH:23]N1C2C=CC=CC=2N=N1.[CH:33]1([N:39]=C=NC2CCCCC2)CCCC[CH2:34]1.C(N(C(C)C)CC)(C)C>C(Cl)Cl>[C:1]([NH:8][CH2:9][C:10]([NH:39][CH2:33][C:34](=[O:23])[NH:16][CH2:15][CH:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[CH3:13])=[O:12])([O:3][C:4]([CH3:5])([CH3:6])[CH3:7])=[O:2]

Participants

7

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 113982-PhenylpropylamineHCID 757711-HydroxybenzotriazoleHCID 78288N-(tert-butoxycarbonyl)glycineHCID 81531Diisopropylethylamine

Product 1

HCID 70212454HCID 70212454, compoundYield 75,882,312%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Boc-glycine (2.1 g, 12 mmol) in methylene chloride (100 mL) was added β-methyl-phenethylamine (1.91 mL, 13.2 mmol), 1-hydroxybenzo-triazole (Hobt) (1.78 g, 13.2 nmol), dicyclohexyl-carbodiimide (DCC) (0.5 M DCC in methylene chloride; 26 mL, 13.2 mmol) and diisopropylethylamine (4.17 mL, 24 mmol). The reaction was stirred at room temperature overnight. The reaction solution was filtered. The filtrate was washed 3 times with brine. The organic solution was dried over MgSO4 and concentrated. Flash chromatography (5% methanol in chloroform) gave 3.5 g (100%) of the title compound as a white solid; CI-MS 293 (m+1).

Workup

  1. filtrationThe reaction solution was filtered
  2. washThe filtrate was washed 3 times with brine
  3. dry with materialThe organic solution was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-65aa9ddd4c08448d8117cb6fa57eda7e
Source dataset
uspto-grants-2001_10
Patent number
US06300501B1

Reaction notes

Loading…