Water → 4-Chloro-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-N-(2-fluoro-4-hydroxymethyl-benzyl)-benzenesulfonamide

HRID 852009Notes

Reaction equation

HRID 852009 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27](O)=[O:28])=[CH:25][C:24]=2[F:32])[C@@H:12]2[CH2:18][C:17]([CH3:20])([CH3:19])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([C@@H:12]2[CH2:18][C:17]([CH3:19])([CH3:20])[CH2:16][CH2:15][NH:14][C:13]2=[O:21])[CH2:22][C:23]2[CH:31]=[CH:30][C:26]([CH2:27][OH:28])=[CH:25][C:24]=2[F:32])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 117127634-{[(4-chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acidHCID 21226445Aluminium lithium hydride

Product 1

HCID 116197334-Chloro-N-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-N-(2-fluoro-4-hydroxymethyl-benzyl)-benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-{[(4-Chloro-benzenesulfonyl)-((R)-5,5-dimethyl-2-oxo-azepan-3-yl)-amino]-methyl}-3-fluoro-benzoic acid (0.05 g, 0.10 mmol) was dissolved in THF (2 ml) and added dropwise to a suspension of LiAlH4 (0.04 g, 1 mmol) in THF (2 ml). After 6 h to the reaction mixture was added water (0.5 ml), 1 N NaOH (0.2 ml) and after 15 min of vigorous stirring it was filtered. The filtrate was concentrated under reduced pressure and purified using preparative RP(C18) chromatography: lyophilisate 5 mg; MS: m/e=469.1 (MH+).

Workup

  1. filtrationwas filtered
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. custompurified

Sources & evidence

ORD record
ord-ac348854050748398b80e88103f91a2c
Source dataset
uspto-grants-2007_08
Patent number
US07253158B2

Reaction notes

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