N-methyl-2-pyrrolidone → HCID 10302535, compound

HRID 1359133Notes

Reaction equation

HRID 1359133 reaction equation
[F:1][C:2]([F:34])([F:33])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([O:16][C:15](=[O:17])[NH:14][CH2:13][CH:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7].CN1C[CH2:39][CH2:38][C:37]1=[O:41].[H-].[Na+].BrCCCO[Si](C(C)(C)C)(C)C.C([O-])(O)=O.[Na+]>>[F:34][C:2]([F:33])([F:1])[C:3]1[CH:4]=[C:5]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[C:6]([N:8]1[CH2:25][CH2:24][C:11]2([O:16][C:15](=[O:17])[N:14]([CH2:39][CH2:38][CH2:37][OH:41])[CH2:13][CH:12]2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:10][CH2:9]1)=[O:7]

Participants

6

Reactant 5

HCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 607486(3-Bromopropoxy)(tert-butyl)dimethylsilaneHCID 10163188HCID 10163188, compound

Product 1

HCID 10302535HCID 10302535, compoundYield 609.7%

Conditions

Temperature
100 °C

Procedure

To a solution of 2.43 g (5 mmol) 9-(3,5-bis-trifluoromethyl-benzoyl)-5-phenyl-1-oxa-3,9-diaza-spiro[5.5]undecan-2-one in N-methylpyrrolidone 0.436 g (0.5 mmol) of a 55% sodium hydride suspension in mineral oil was added at room temperature under argon. After 15 min. 1.27 g (5 mmol) of (3-bromopropoxy)-tert-butyldimethylsilane was added. The reaction mixture was stirred at 100° C. under argon overnight. After cooling a solution of saturated aqueous NaHCO3 was added and the mixture was extracted with ethyl acetate. The organic layer was dried over (Na2SO4) and concentrated. The residue was purified by column chromatography (SiO2, Hexane/ethylacetate=2:1) to yield 1.66 g (50%) of a yellow oil.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography (SiO2, Hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-6192df9538d74c69bc6f5ed3ea3e8603
Source dataset
uspto-grants-2003_07
Patent number
US06599900B2

Reaction notes

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