Dicyclohexylcarbodiimide → HCID 23387542, compound

HRID 1170625Notes

Reaction equation

HRID 1170625 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=1)=[O:10].C1CCC(N=C=NC2CCCCC2)CC1.CN(C1C=CC=CN=1)C.[C:45]([NH:55][C@H:56]([C:60](O)=[O:61])[CH:57]([CH3:59])[CH3:58])([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46]>ClCCl>[C:45]([NH:55][C@H:56]([C:60]([O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=1)=[O:10])=[O:61])[CH:57]([CH3:59])[CH3:58])([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 726987N-Carbobenzoxy-L-valineHCID 22035799HCID 22035799, compound

Product 1

HCID 23387542HCID 23387542, compoundYield 93.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methoxybenzyl 2-hydroxyphenylacetate 3 g, 11 mmol), N,N,-dichyclohexyl-carbodiimide (2.7 g, 13.2 mmol), dimethylaminopyridine (0.134 g, 1.1 mmol) and CBz-L-valine (3.3 g, 13.2 mmol) were dissolved in dichloromethane (50 ml). After the weekend the solid was filtered off, the solvent removed under reduced pressure and the crude product purified by chromatography (ethyl acetate, hexane, 1:2) to give the title compound (5.2 g, 93%).

Workup

  1. filtrationAfter the weekend the solid was filtered off
  2. customthe solvent removed under reduced pressure
  3. customthe crude product purified by chromatography (ethyl acetate, hexane, 1:2)

Sources & evidence

ORD record
ord-a2b4ed418d204256bb07fa5bd95ac3db
Source dataset
uspto-grants-2010_11
Patent number
US07825238B2

Reaction notes

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