Sodium Hydroxide → HCID 59263290, compound

HRID 643992Notes

Reaction equation

C[O:2][C:3](=[O:43])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[CH:6][C:5]=1[N:11]([S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH2:29][CH2:30][C:31]2[N:32]=[C:33]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)[O:34][C:35]=2[CH3:36])=[CH:24][CH:23]=1)(=[O:21])=[O:20])C(OC(C)(C)C)=O.[OH-].[Na+]>O1CCOCC1>[Cl:10][C:7]1[CH:8]=[CH:9][C:4]([C:3]([OH:43])=[O:2])=[C:5]([NH:11][S:19]([C:22]2[CH:23]=[CH:24][C:25]([O:28][CH2:29][CH2:30][C:31]3[N:32]=[C:33]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[O:34][C:35]=3[CH3:36])=[CH:26][CH:27]=2)(=[O:20])=[O:21])[CH:6]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of the title G compound, 4-chloro-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzenesulfonyl-(t-butoxycarbonyl)amino}-benzoic acid methyl ester (300 mg, 0.48 mmol) in dioxane (5 mL) to which 2.4 mL of 1 N aqueous NaOH is added is heated at 90° C. for 3 h. The mixture is concentrated under vacuum, acidified with 1 N aqueous HCl, and extracted twice with EtOAc. The organic solution is dried over anhydrous magnesium sulfate, filtered and concentrated to give a crude product which is triturated with DCM. The solid is collected by filtration to afford 4-chloro-2-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzenesulfonyl-amino}-benzoic acid: m.p. 223-225° C.; ESI-MS 513 [M+1]+.

Workup

concentrationThe mixture is concentrated under vacuum
extractionextracted twice with EtOAc
dry with materialThe organic solution is dried over anhydrous magnesium sulfate
filtrationfiltered
concentrationconcentrated
customto give a crude product which
customis triturated with DCM
filtrationThe solid is collected by filtration

Sources & evidence

ORD record: ord-51ab0df35d444a858001de495f719a74
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700637B2

Reaction notes

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