Sodium hydride → HCID 59717868, compound

HRID 2197649Notes

Reaction equation

HRID 2197649 reaction equation
[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].F[C:21]1[CH:26]=[CH:25][C:24]([S:27]([N:30]=[N+:31]=[N-:32])(=[O:29])=[O:28])=[CH:23][CH:22]=1.C(OC(=O)NCCC1C=CC(OS(C2C=CC(F)=CC=2)(=O)=O)=CC=1)(C)(C)C>CN(C=O)C>[C:1]([O:5][C:6](=[O:17])[NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([O:16][C:21]2[CH:26]=[CH:25][C:24]([S:27]([N:30]=[N+:31]=[N-:32])(=[O:29])=[O:28])=[CH:23][CH:22]=2)=[CH:12][CH:11]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamateHCID 152559014-Fluorobenzene-1-sulfonyl azideHCID 86760676HCID 86760676, compound

Product 1

HCID 59717868HCID 59717868, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Dissolve [2-(4-hydroxyphenyl)ethyl]carbamic acid tert-butyl ester (0.594 g, 2.50 mmol) in DMF (12.5 mL). Add NaH (80% in mineral oil) (0.083 g, 2.75 mmol). Stir at room temperature for 30 minutes. Add 4-fluorobenzenesulfonyl azide (0.504 g, 2.50 mmol) and heat to 60° C. Remove DMF as an azeotrope with xylenes after 3.75 hours. Purify by flash 40 chromatography, eluting with 30% ethyl acetate in hexanes to give a mixture of (2-(4-(4-fluorobenzenesulfonyl)oxyphenyl)ethyl)carbamic acid tert-butyl ester and the title compound: HPLC [YMC-Pack Pro C-18 (150×4.6 mm, S-5 microm), acetonitrile in water containing 0.01% concentrated HCl at 1.0 mL/min, 50-99% over 19 min], tR=16.1 min, 35% purity; TLC [silica gel 60 F254, 5% ethyl acetate in hexanes] Rf=0.49.

Workup

  1. customPurify by flash 40 chromatography
  2. washeluting with 30% ethyl acetate in hexanes
  3. customto give

Sources & evidence

ORD record
ord-2e2b1684839a44f6879812214b08341e
Source dataset
uspto-grants-2012_12
Patent number
US08338611B2

Reaction notes

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