Dicyclohexylcarbodiimide → HCID 23387542, compound

HRID 1790790Notes

Reaction equation

HRID 1790790 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-b2dfc0b229c6457b8b7e3ffde9156c9d
Source dataset
uspto-grants-2006_07
Patent number
US07071173B2

Reaction notes

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