2-Dimethylaminopyridine → HCID 23387542, compound

HRID 989968Notes

Reaction equation

HRID 989968 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].CN(C1C=CC=CN=1)C.[C:30]([NH:40][C@H:41]([C:45](O)=[O:46])[CH:42]([CH3:44])[CH3:43])([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]>ClCCl>[C:30]([NH:40][C@H:41]([C:45]([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:46])[CH:42]([CH3:44])[CH3:43])([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31]

Participants

5

Reactant 3

HCID 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,-dicyclohexyl-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-a870952379ee430cb8ccc1ca132d8b47
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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