2-Mercaptoethanol → HCID 69883783, compound

HRID 2120349Notes

Reaction equation

[Cl:1][C:2]1[C:7](F)=[C:6]([S:9]([C:12]2[CH:17]=[CH:16][C:15]([C:18](=[O:22])[N:19]([CH3:21])[CH3:20])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:23][C:24](=[O:32])[C@:25]([OH:31])([CH3:30])[C:26]([F:29])([F:28])[F:27].[OH:33][CH2:34][CH2:35][SH:36].C[O-].[Na+]>CN1C(=O)CCC1.[Cl-].[Na+].O>[Cl:1][C:2]1[C:7]([S:36][CH2:35][CH2:34][OH:33])=[C:6]([S:9]([C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:22])[N:19]([CH3:20])[CH3:21])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][C:3]=1[NH:23][C:24](=[O:32])[C@:25]([OH:31])([CH3:30])[C:26]([F:28])([F:27])[F:29]

Participants

Conditions

Temperature: 120 °C

Procedure

To (R)-N-{2-chloro-3-fluoro-4-[4-(N,N-dimethylcarbamoyl)phenylsulphonyl]phenyl}-2-hydroxy-2-methyl-3,3,3-trifluoropropanamide (Example 18) (600 mg), as a solution in NMP (5 ml), was added 2-hydroxyethanethiol (0.1 ml) and sodium methoxide (0.65 g), and the reaction mixture was heated at 120° C. overnight under an argon atmosphere. The solution was diluted with saturated brine and extracted with ether (3×30 ml). The ether extracts were combined and dried. The volatile material was removed by evaporation and purified by chromatography on a Mega Bond Elut column (20 g silica) eluting with hexane/EtOAc to yield the title compound as a white solid (60 mg, 12%). NMR: 1.60 (s, 3H), 2.60-2.65 (m, 2H),), 2.85 (s, 3H), 2.95 (s, 3H), 3.10-3.20 (m, 2H), 4.75 (dd, 1H), 7.60 (d, 2H); 7.95 (d, 2N), 8.05 (s, 1H), 8.35 (d, 1H), 8.45 (d, 1H), 9.95 (s, 1H); m/z: 553.

Workup

extractionextracted with ether (3×30 ml)
customdried
customThe volatile material was removed by evaporation
custompurified by chromatography on a Mega Bond Elut column (20 g silica)
washeluting with hexane/EtOAc

Sources & evidence

ORD record: ord-e201955513ac4c65ac52493e6e7b0b9c
Source dataset: uspto-grants-2004_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06689909B1

Reaction notes

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