Ethanol → HCID 86742759, compound

HRID 1382710Notes

Reaction equation

HRID 1382710 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 86742760HCID 86742760, compound

Product 1

HCID 86742759HCID 86742759, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.9 g (0.023 mol) of (±)-(S*,R*)-β-[(1-amino-2-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid methyl ester, 50 ml ethanol and 140 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 (2×75 ml). The aqueous solution was chilled, then neutralized with acetic acid and extracted with ethyl acetate (3×75 ml). The combined extracts were washed with water (75 ml) and dried (MgSO4). Removal of the solvent gave 8.2 g (96%) of (±)-(S*,R*)-β-[(1-amino-2-naphthalenyl)thio]-α-hydroxy-4-methoxybenzenepropanoic acid, mp 167°-168°. The analyzed sample was recrystallized from ethyl acetate, mp 167°-168°.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 30 minutes
  3. extractionextracted with ether (2×75 ml)
  4. temperatureThe aqueous solution was chilled
  5. extractionextracted with ethyl acetate (3×75 ml)
  6. washThe combined extracts were washed with water (75 ml)
  7. dry with materialdried (MgSO4)
  8. customRemoval of the solvent

Sources & evidence

ORD record
ord-c21336d9134347c6baeeccbd52b2faa7
Source dataset
uspto-grants-1989_02
Patent number
US04808580

Reaction notes

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