Ethanol → HCID 86742761, compound

HRID 1382711Notes

Reaction equation

HRID 1382711 reaction equation
C[O:2][C:3](=[O:27])[C@@H:4]([OH:26])[C@H:5]([S:14][C:15]1[CH:24]=[CH:23][C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]=1[NH2:25])[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[CH:8][CH:7]=1.C(O)C.[OH-].[Na+]>O>[NH2:25][C:16]1[C:17]2[C:22](=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:23]=[CH:24][C:15]=1[S:14][C@H:5]([C:6]1[CH:7]=[CH:8][C:9]([O:12][CH3:13])=[CH:10][CH:11]=1)[C@H:4]([OH:26])[C:3]([OH:27])=[O:2]

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 53677992HCID 53677992, compound

Product 1

HCID 86742761HCID 86742761, compoundYield 87.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.6 g (0.017 mol) of (±)-(R*,R*)-β-[(1-amino-2-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid methyl ester, 45 ml ethanol and 100 ml 1N sodium hydroxide was heated at reflux for 30 minutes. The reaction mixture was cooled to room temperature, diluted with water (50 ml) and extracted with ether. The aqueous solution was chilled, then neutralized with acetic acid and extracted with ethyl acetate (3×60 ml). The combined extracts were washed with water (50 ml) and dried (MgSO4). Removal of the solvent gave 5.5 g of crude (±)-(R*,R*)-β-[(1-amino-2-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid which was dissolved in methylene chloride and chromatographed on a column using 55 g of silica gel. The column was eluted with 50 ml portions of methylene chloride. Fractions 12-17 were collected, and the solvent was removed under reduced pressure to afford 1.3 g (20%) of (±)-(R*,R*)-β-[(1-amino-2-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid. The analyzed sample was recrystallized from ether, mp 160°-161°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. extractionextracted with ether
  4. temperatureThe aqueous solution was chilled
  5. extractionextracted with ethyl acetate (3×60 ml)
  6. washThe combined extracts were washed with water (50 ml)
  7. dry with materialdried (MgSO4)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-d5dcdd8ee6af4ae2a3a21558001dad4b
Source dataset
uspto-grants-1989_02
Patent number
US04808580

Reaction notes

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