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

HRID 1604717Notes

Reaction equation

HRID 1604717 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>[OH:17][CH2:16][CH2:15][CH2:14][CH2:13][C@H:7]([N:12]1[C:13](=[O:22])[C:14]2[C:15](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:16]1=[O:17])[C:1]([OH:4])=[O:2]

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 (1.030 g, 7.0 mmol): ##STR28## prepared by the method of Bodanszky, M. et al., J. Med. Chem., 21, 1030-1035 (1978), and Na2CO3 (745 mg, 7.0 mmol) in H2O (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 HCl to afford a white precipitate. The solid was collected by filtration and dried in vacuo at 80° C. for 1 hour to give the title compound of this step as a pure acid (1.297 g, 67%).

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 1 hour

Sources & evidence

ORD record
ord-459bc8c16b4f4626b9b715c319a800fd
Source dataset
uspto-grants-1999_11
Patent number
US05994537

Reaction notes

Loading…