Sodium Carbonate → (S)-2-Phthalimido-6-hydroxyhexanoic acid

HRID 52800

Reaction equation

HRID 52800 reaction equation
[C:1](=[O:4])([O-])[O-:2].[Na+].[Na+].[C:7]([N:12]1[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]2[C:13]1=[O:22])(OCC)=O>O>[C:13]1(=[O:22])[N:12]([C@@H:7]([CH2:13][CH2:14][CH2:15][CH2:16][OH:17])[C:1]([OH:2])=[O:4])[C:16](=[O:17])[C:15]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:14]12

Participants

4

Reactant 2

HCID 10340Sodium CarbonateHCID 31187N-Carbethoxyphthalimide

Product 1

HCID 11065730(S)-2-Phthalimido-6-hydroxyhexanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of (+)-L-ε-hydroxynorleucine [prepared according to the procedure of Bodanszky et al., J. Med Chem., 1978, 21, 1030-1035] (1.030 g., 7.0 mmol.) and sodium carbonate (745 mg., 7.0 mmol.) in water (12 ml.) was treated with N-carbethoxyphthalimide (1.495 g., 7.0 mmol.) and the mixture was stirred at room temperature for 2 hours. The solution was filtered, cooled to 0° C., and acidified with 6N hydrochloric acid to afford a white precipitate. The solid was collected by filtration and dried in vacuo at 80° C. for one hour to give 1.297 g. of the title compound; m.p. 162°-163° C.; [α]D =-35.7° (c=1.3, methanol).

Workup

  1. filtrationThe solution was filtered
  2. temperaturecooled to 0° C.
  3. customto afford a white precipitate
  4. filtrationThe solid was collected by filtration
  5. customdried in vacuo at 80° C. for one hour
  6. customto give 1.297 g

Sources & evidence

ORD record
ord-a31934291ca1485ab668aa7825a09a76
Source dataset
uspto-grants-1997_04
Patent number
US05616775

Linked notes

Loading…