Dicyclohexylcarbodiimide → HCID 23387528, compound

HRID 1170618Notes

Reaction equation

HRID 1170618 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:19][C:20]([CH3:25])([CH2:23]O)[CH2:21][OH:22].C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C(Cl)Cl>[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:16]([O:18][CH2:19][C:20]([CH3:25])([CH3:23])[CH2:21][OH:22])=[O:17])[CH:13]([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 31344Neopentyl glycolHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 23387528HCID 23387528, compoundYield 88.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-benzyloxycarbonyl-L-valine (2.50 g, 10.0 mmol), 2,2-dimethyl-1,3-propanediol (5.30 g, 50.9 mmol), dicyclohexylcarbodiimide (2.60 g, 12.6 mmol), and 4-dimethylaminopyridine (125 mg, 1.0 mmol) in 100 mL dry CH2Cl2 was stirred for 23 h. The reaction mixture was filtered and washed successively with 50 mL each of water, saturated aqueous NH4Cl, saturated aqueous NaHCO3, and water. The organic phase was dried over anhydrous Na2SO4 and concentrated. The title compound (2.99 g, 87%) was isolated by flash column chromatography (silica, 2/1 petroleum ether-ethyl acetate) as a white waxy solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washwashed successively with 50 mL each of water, saturated aqueous NH4Cl, saturated aqueous NaHCO3, and water
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b66301a2283e4ee4b4e8ef958dbfbe89
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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