Dicyclohexylcarbodiimide → HCID 59364371, compound

HRID 426052Notes

Reaction equation

HRID 426052 reaction equation
[C:1]([O:5][C:6]([N:8]([CH3:13])[CH2:9][C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:16]=[C:17]([NH:21][CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:29])[O:27][CH3:28])[CH:18]=[CH:19][CH:20]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[Cl:14][C:15]1[CH:16]=[C:17]([N:21]([CH2:22][CH2:23][CH2:24][NH:25][C:26]([O:27][CH3:28])=[O:29])[C:10](=[O:12])[CH2:9][N:8]([CH3:13])[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])[CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 83692Glycine, N-[(1,1-dimethylethoxy)carbonyl]-N-methyl-HCID 59364341HCID 59364341, compound

Product 1

HCID 59364371HCID 59364371, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(tert-butoxycarbonyl(methyl)amino)acetic acid in CH2Cl2 at 0° C. under argon atmosphere was added DMAP, methyl 3-(3-chlorophenylamino)propylcarbamate and DCC. The reaction mixture was allowed to stir at room temperature for 24 h. The resulting suspension was filtered, the filtrate concentrated under reduced pressure and the crude residue was subjected to silica gel chromatography to give tert-butyl 2-((3-chlorophenyl)(3-(methoxycarbonylamino)propyl)amino)-2-oxoethyl(methyl)carbamate. 1H NMR δ 0.7-0.9 (m, 4H), 1.0-1.15 (m, 1H), 1.3 (s, 3H), 1.4 (s, 9H), 1.65 (m, 2H), 2.85 (m, 3H), 3.7 (m, 4H), 3.75 (m, 2H), 5.65 (m, 1H), 7.0-7.2 (m, 1H), 7.25 (m, 2H), 7.4 (m, 2H).

Workup

  1. filtrationThe resulting suspension was filtered
  2. concentrationthe filtrate concentrated under reduced pressure

Sources & evidence

ORD record
ord-07e08d5c0f484bddac900c19406f7fa9
Source dataset
uspto-grants-2012_01
Patent number
US08106221B2

Reaction notes

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