Sodium Hydroxide → HCID 59643436, compound

HRID 2251543Notes

Reaction equation

[CH3:1][S:2]([N:5](S(C)(=O)=O)[C:6]1[CH:7]=[CH:8][C:9]([N:12]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:39])[F:38])=[CH:33][CH:32]=2)[CH2:13][CH2:14][C:15]2[CH:29]=[CH:28][C:18]([O:19][C:20]([CH3:27])([CH3:26])[C:21]([O:23]CC)=[O:22])=[CH:17][CH:16]=2)=[N:10][CH:11]=1)(=[O:4])=[O:3].[OH-].[Na+]>>[CH3:27][C:20]([O:19][C:18]1[CH:28]=[CH:29][C:15]([CH2:14][CH2:13][N:12]([C:9]2[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])=[CH:11][N:10]=2)[CH2:30][C:31]2[CH:36]=[CH:35][C:34]([C:37]([F:40])([F:38])[F:39])=[CH:33][CH:32]=2)=[CH:16][CH:17]=1)([CH3:26])[C:21]([OH:23])=[O:22]

Participants

Reactant 2

HCID 14798Sodium Hydroxide

HCID 69099565HCID 69099565, compound

Product 1

HCID 59643436HCID 59643436, compoundYield 66%

Procedure

Ethyl 2-[4-(2-{{5-[bis(methylsulfonyl)amino]pyridin-2-yl}[4-(trifluoromethyl)benzyl]amino}ethyl)phenoxy]-2-methylpropanoate (39 mg) was reacted with NaOH (17 eq) as per general procedure H. Purification by radial chromatography (1–10% methanol-dichloromethane gradient), followed by crystallization from dichloromethane-hexane afforded the title compound as a white solid (21 mg; 66% yield).

Workup

customPurification by radial chromatography (1–10% methanol-dichloromethane gradient)
customfollowed by crystallization from dichloromethane-hexane

Sources & evidence

ORD record: ord-fd4d0f7aeda74f14b21b47b094e32526
Source dataset: uspto-grants-2008_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07319104B2

Reaction notes

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