Hydrochloric Acid → (4R)-N-[4-(4'-chlorobiphenyl-4-sulfonylamino)-4-carboxybutyl]phthalamic acid

HRID 651325Notes

Reaction equation

HRID 651325 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@H:18]([CH2:22][CH2:23][CH2:24][N:25]3[C:33](=[O:34])[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[C:26]3=[O:35])[C:19]([OH:21])=[O:20])(=[O:16])=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.ClC1(S(N[C@H](CCCN2C(=O)C3C(=CC=CC=3)C2=O)C(O)=O)(=O)=[O:50])C=CC(C2C=CC=CC=2)=CC1.[OH-].[Li+].Cl>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([NH:17][C@@H:18]([C:19]([OH:21])=[O:20])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[O:35])[C:27]3[C:32](=[CH:31][CH:30]=[CH:29][CH:28]=3)[C:33]([OH:50])=[O:34])(=[O:15])=[O:16])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 15549671(2R)-(4'-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acidHCID 70237707(2R)-(4-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid

Product 1

HCID 59965684(4R)-N-[4-(4'-chlorobiphenyl-4-sulfonylamino)-4-carboxybutyl]phthalamic acidYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the title compound of Example 1, (2R)-(4-chlorobiphenyl-4-sulfonylamino)-5-(1,3-dioxo-1,3-dihydroisoindol-2-yl)pentanoic acid (20.0 mg, 0.039 mmol), in 2 mL of tetrahydrofuran is treated with 1M aqueous lithium hydroxide. After 2 h, the solution is acidified with 0.2 mL of 1N aqueous HCl, and the mixture is concentrated to an oil. Chomatography on LiChoprep DIOL (eluant; ethyl acetate) affords 12.8 mg (62%) of (4R)-N-[4-(4′-chlorobiphenyl-4-sulfonylamino)-4-carboxybutyl]phthalamic acid as a white solid: m.p. 119-121° C. (dec); IR 1737, 1701, 1649, 1344, 1168; ESI-MS 529 (M−−1).

Workup

  1. concentrationthe mixture is concentrated to an oil

Sources & evidence

ORD record
ord-d252f547668e4b888ac7e57b22d1be61
Source dataset
uspto-grants-2001_08
Patent number
US06277987B1

Reaction notes

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