Resorcinol → HCID 23387532, compound

HRID 989966Notes

Reaction equation

HRID 989966 reaction equation
[C:1]([NH:11][C@H:12]([C:16]([OH:18])=[O:17])[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[OH:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22](O)[CH:21]=1>CN(C)C1C=CN=CC=1.CN(C=O)C>[C:1]([NH:11][C@H:12]([C:16]([O:18][C:22]1[CH:21]=[C:20]([OH:19])[CH:25]=[CH:24][CH:23]=1)=[O:17])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2]

Participants

5

Reactant 2

HCID 5054ResorcinolHCID 726987N-Carbobenzoxy-L-valine

Product 1

HCID 23387532HCID 23387532, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

CBz-L-valine (10 g, 40 mmol), 1,3-dihydroxybenzene (8.7 g, 79 mmol) N,N′dicychlohexylcarbodiimide (10.2 g, 44 mmol) and 4-dimethylaminopyridine (2.4 g, 20 mmol) were dissolved in DMF (50 ml) and left at ambient temperature overnight. The reaction mixture was filtered, the solvent removed under reduced pressure and the crude product was taken up in dichloromethane and filtered. Removal of the solvent followed by purification by chromatography (chloroform-methanol, 10:1) yielded pure title product (10.9 g, 79%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent removed under reduced pressure
  3. filtrationfiltered
  4. customRemoval of the solvent
  5. customfollowed by purification by chromatography (chloroform-methanol, 10:1)

Sources & evidence

ORD record
ord-e36fab5727374c2c83d461747d51e5bc
Source dataset
uspto-grants-2002_10
Patent number
US06458772B1

Reaction notes

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