Sodium hydride → HCID 15614947, compound

HRID 620361Notes

Reaction equation

HRID 620361 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[C:6]([C:29]([F:32])([F:31])[F:30])=[C:7]2[C:12](=[CH:13][CH:14]=1)[C:11]([C:15]([NH:17][C:18](=[O:22])[O:19][CH2:20][CH3:21])=[O:16])=[C:10]([O:23][CH2:24][C:25]([F:28])([F:27])[F:26])[CH:9]=[CH:8]2.Br[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36]>O1CCCC1>[CH2:20]([O:19][C:18]([N:17]([C:15]([C:11]1[C:12]2[C:7](=[C:6]([C:29]([F:31])([F:30])[F:32])[C:5]([O:4][CH3:3])=[CH:14][CH:13]=2)[CH:8]=[CH:9][C:10]=1[O:23][CH2:24][C:25]([F:26])([F:27])[F:28])=[O:16])[CH2:34][C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 15614952HCID 15614952, compound

Product 1

HCID 15614947HCID 15614947, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

Sodium hydride (80% by weight dispersion in mineral oil, 0.346 g, 1.1 eq) was added to a stirred solution of N-[[6-methoxy-2-(2,2,2-trifluoroethoxy)-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]carbamic acid, ethyl ester (4.60 g, 10.5 mmol) in anhydrous tetrahydrofuran (125 mL) at room temperature under a dry nitrogen atmosphere. After 1 hour, the t-butyl bromoacetate (2.54 mL, 1.5 eq) was added. The reaction was heated to 65° C. for 1 hour, cooled to room temperature, and the THF was removed. The residue was dissolved in ether (200 mL), washed with water (2×50 mL) and saturated aqueous NaCl (1×50 mL). The ether phase was dried with magnesium sulfate and the ether was removed. The crude product was flash chromatographed (17:3 petroleum ether:ethyl acetate, silica) and triturated with petroleum ether to provide the title compound as a white powder (4.60 g, 79%), m.p. 84°-86° C.

Workup

  1. temperaturecooled to room temperature
  2. customthe THF was removed
  3. dissolutionThe residue was dissolved in ether (200 mL)
  4. washwashed with water (2×50 mL) and saturated aqueous NaCl (1×50 mL)
  5. dry with materialThe ether phase was dried with magnesium sulfate
  6. customthe ether was removed
  7. customchromatographed (17:3 petroleum ether:ethyl acetate, silica)
  8. customtriturated with petroleum ether

Sources & evidence

ORD record
ord-0e900318c51e447b9c0b7a8b1d31d132
Source dataset
uspto-grants-1989_04
Patent number
US04820727

Reaction notes

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