Diisopropylcarbodiimide → Allyl {2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethyl}carbamate

HRID 1670497Notes

Reaction equation

HRID 1670497 reaction equation
CC(C)N=C=NC(C)C.[CH2:10]([O:13][C:14]([NH:16][CH:17]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1)[C:18]([OH:20])=O)=[O:15])[CH:11]=[CH2:12].[CH2:29]([O:31][CH:32]([O:38][CH2:39][CH3:40])[CH2:33][NH:34][CH:35]([CH3:37])[CH3:36])[CH3:30].C1C=NC2N(O)N=NC=2C=1>CN(C=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([CH2:21][CH:17]([NH:16][C:14](=[O:15])[O:13][CH2:10][CH:11]=[CH2:12])[C:18](=[O:20])[N:34]([CH2:33][CH:32]([O:31][CH2:29][CH3:30])[O:38][CH2:39][CH3:40])[CH:35]([CH3:36])[CH3:37])=[CH:23][CH:24]=1

Participants

6

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 181649HOAtHCID 12503262N-(2,2-diethoxyethyl)propan-2-amineHCID 673396363-(4-Chlorophenyl)-2-{[(prop-2-en-1-yloxy)carbonyl]amino}propanoic acid

Product 1

HCID 86597579Allyl {2-(4-chlorophenyl)-1-[(2,2-diethoxyethyl)isopropylcarbamoyl]ethyl}carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.8 ml of DIC are added dropwise to a solution of 5.7 g of 2-allyloxycarbonylamino-3-(4-chlorophenyl)propionic acid, 3.5 g of (2,2-diethoxyethyl)isopropylamine, 6.8 g of HOAt in 30 ml of DMF and the solution is stirred for 12 h. The reaction solution is concentrated under reduced pressure and purified by flash chromatography on silica gel (eluent ethyl acetate/n-heptane=1/3). The desired product is obtained with MW=440.97 (calculated monoisotopic); measured value (M+H)+: 441.15

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. custompurified by flash chromatography on silica gel (eluent ethyl acetate/n-heptane=1/3)

Sources & evidence

ORD record
ord-af216829cb204b0da80e52d72bb2306c
Source dataset
uspto-grants-2011_08
Patent number
US07994168B2

Reaction notes

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