L-Phenylalanine → Phenylalanine sodium

Reaction equation

[NH2:1][C@H:2]([C:10]([OH:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[OH-].[Na+:14]>>[Na+:14].[NH2:1][C@H:2]([C:10]([O-:12])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

Reactant 2

HCID 6140L-Phenylalanine

HCID 14798Sodium Hydroxide

Product 1

HCID 23677936Phenylalanine sodium

Procedure

A solution of N-(2-chloro-6-methylbenzoyl)-4-[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine (0.15 g) in 1.0 N NaOH (0.3 mL) was applied to a 2×20 cm open column of C-18 reversed phase silica gel (40-63 μM, RP Silica Gel60, as supplied by EM Separations, Cat. 10167) eluting with water, then with 40-50% methanol in water to give N-(2-chloro-6-methylbenzoyl)-4-[(2,6-dichlorophenyl)carbonyl]amino]-L-phenylalanine sodium salt (147 mg) as an amorphous white solid after lyophilization.

Workup

washeluting with water

Sources & evidence

ORD record: ord-67b606452e124691a9cbece301ac3167
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06229011B1

Reaction notes

Loading…