Sodium hydride → HCID 15614943, compound

HRID 620350Notes

Reaction equation

HRID 620350 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:17])([F:16])[F:15])[C:5]=1[C:20]([NH:22][C:23](=[O:27])[O:24][CH2:25][CH3:26])=[O:21].Br[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31]>O1CCCC1>[F:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:16])([F:17])[F:15])[C:5]=1[C:20]([N:22]([C:23]([O:24][CH2:25][CH3:26])=[O:27])[CH2:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])=[O:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 15614950HCID 15614950, compound

Product 1

HCID 15614943HCID 15614943, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (80% by weight dispersion in mineral oil 0.208 g, 1.1 eq) was added to a stirred solution of N-[[2-fluoro-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]carbamic acid, ethyl ester (2.26 g, 6.29 mmol) in anhydrous tetrahydrofuran (75 mL) at room temperature under a dry nitrogen atmosphere. After 45 minutes, the t-butyl bromoacetate (1.52 mL, 1.5 eq) was added and the reaction was heated to 60° C. After 11/4 hours of heating, the reaction was cooled to room temperature and the THF was removed. The residue was suspended in ether (150 mL), washed with water (2×75 mL) and saturated aqueous NaCl (1×50 mL), dried with MgSO4, and the ether was removed. The crude oil was flash chromatographed (4:1 petroleum ether:ethyl acetate, silica) then triturated with petroleum ether (3×30 mL) to provide the title compound as a white powder (2.40 g, 81%), m.p. 81°-83° C.

Workup

  1. temperatureAfter 11/4 hours of heating
  2. temperaturethe reaction was cooled to room temperature
  3. customthe THF was removed
  4. washwashed with water (2×75 mL) and saturated aqueous NaCl (1×50 mL)
  5. dry with materialdried with MgSO4
  6. customthe ether was removed
  7. customchromatographed (4:1 petroleum ether:ethyl acetate, silica)
  8. customthen triturated with petroleum ether (3×30 mL)

Sources & evidence

ORD record
ord-bd2eb28361464764b34ce9eab80a42c5
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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