phenylalaninol, (S)- → HCID 17751795, compound

HRID 498930

Reaction equation

HRID 498930 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([OH:19])=[C:13]([CH:18]=1)[C:14]([O:16]C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C@@H:21]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:22][OH:23]>CN(C)C=O.C(OCC)(=O)C.CCCCCC>[OH:23][CH2:22][C@@H:21]([NH:20][C:14](=[O:16])[C:13]1[CH:18]=[C:9]([O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:10]=[CH:11][C:12]=1[OH:19])[CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 2

HCID 447213phenylalaninol, (S)-HCID 13026913Methyl 5-(benzyloxy)-2-hydroxybenzoate

Product 1

HCID 17751795HCID 17751795, compoundYield 50%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a flask equipped with a reflux condenser and a magnetic stirring bar are dissolved the methyl 5-benzyloxy-2-hydroxybenzoate and one equivalent of 2-(S)-amino-3-phenyl-1-propanol in dry dimethyl formamide. The flask is immersed in an oil bath at 75° C. and left to stir for 72 hours. The solvent is evaporated and the residue is isolated-through the use of a silica gel column using a mixture of ethyl acetate and hexane as eluent. In this fashion is obtained in 50% yield, N-{(S)-1-hydroxy-3-phenyl-2-propyl}-5-benzyloxy-2-hydroxybenzamide.

Workup

  1. customIn a flask equipped with a reflux condenser and a magnetic stirring bar
  2. customThe flask is immersed in an oil bath at 75° C.
  3. waitleft
  4. customThe solvent is evaporated
  5. customthe residue is isolated-through the use of a silica gel column

Sources & evidence

ORD record
ord-2e9df2b5b2534b7b95ac125dc68089f9
Source dataset
uspto-grants-2010_08
Patent number
US07767646B2

Linked notes

Loading…