Isonicotinic Acid → HCID 513996, compound

HRID 987987Notes

Reaction equation

[NH2:1][C@@H:2]([CH:28]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][C@H:10]([N:13]([S:18]([C:21]1[CH:26]=[CH:25][C:24]([NH2:27])=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:11][OH:12])=[O:4].[C:41](O)(=[O:48])[C:42]1[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=1.[OH-].[Na+]>>[NH2:27][C:24]1[CH:23]=[CH:22][C:21]([S:18]([N:13]([CH2:14][CH:15]([CH3:17])[CH3:16])[C@H:10]([CH2:11][OH:12])[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:3]([C@@H:2]([NH:1][C:41](=[O:48])[C:42]2[CH:47]=[CH:46][N:45]=[CH:44][CH:43]=2)[CH:28]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:4])(=[O:20])=[O:19])=[CH:26][CH:25]=1

Participants

Reactant 3

HCID 5922Isonicotinic Acid

HCID 14798Sodium Hydroxide

HCID 513994HCID 513994, compound

Product 1

HCID 513996HCID 513996, compound

Procedure

The title compound was then obtained in 76% yield using (2S,5S)-2-amino-N-{5-[(4-amino-benzenesulfonyl)-isobutyl-amino]-6-hydroxy-hexyl}-3,3-diphenyl-propionamide (product of example 72) and isonicotinic acid with general procedure A. However, 1.0N NaOH was used instead of 1.0N hydrochloric acid for the preparation of the title compound.

Sources & evidence

ORD record: ord-b6e73dce0dd049d998e8c8ca18b5ccd4
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06632816B1

Reaction notes

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