Tetrahydrofuran → HCID 135999735, compound

HRID 1157967Notes

Reaction equation

HRID 1157967 reaction equation
[CH3:1][O:2][C:3]([C:5]1[O:9][CH:8]=[N:7][C:6]=1[N:10]1[C:14](=[O:15])[NH:13][C:12]([CH:16]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([CH2:49][NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH:42]=2)[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH2:26][CH2:27][O:28][Si](C(C)C)(C(C)C)C(C)C)[C:18]=2[F:39])=[N:11]1)=[O:4].C1COCC1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>O>[CH3:1][O:2][C:3]([C:5]1[O:9][CH:8]=[N:7][C:6]=1[N:10]1[C:14](=[O:15])[NH:13][C:12]([CH:16]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([C:47]#[N:48])=[C:43]([CH2:49][NH:50][C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[CH:42]=2)[C:17]2[CH:22]=[C:21]([O:23][CH3:24])[CH:20]=[C:19]([O:25][CH2:26][CH2:27][OH:28])[C:18]=2[F:39])=[N:11]1)=[O:4]

Participants

6

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 136011089HCID 136011089, compound

Product 1

HCID 135999735HCID 135999735, compoundYield 117.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 4-(3-{[3-(t-butoxycarbonylaminomethyl)-4-cyanophenylamino]-[2-fluoro-5-methoxy-3-(2-triisopropylsilanyloxyethoxy)phenyl]methyl}-5-oxo-4,5-dihydro-[1,2,4]triazol-1-yl)oxazole-5-carboxylic acid methyl ester (41.1 mg) and THF (2 mL) there was added a 1M THF solution of tetrabutylammonium fluoride (0.100 mL). The mixture was stirred for 3 hours, and then ethyl acetate (30 mL) and water (15 mL) were added. The mixture was sufficiently shaken, and then the organic layer was separated off, washed with water (15 mL) and saturated aqueous sodium chloride (15 mL) in that order, and dried over anhydrous magnesium sulfate. The mixture was filtered to obtain a filtrate and the solvent in the filtrate was distilled off under reduced pressure to obtain the target compound (39.1 mg) as a colorless oil.

Workup

  1. stirringThe mixture was sufficiently shaken
  2. customthe organic layer was separated off
  3. washwashed with water (15 mL) and saturated aqueous sodium chloride (15 mL) in that order
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe mixture was filtered
  6. customto obtain a filtrate
  7. distillationthe solvent in the filtrate was distilled off under reduced pressure

Sources & evidence

ORD record
ord-1ad69394c3cc4979b7df78586a5a2df0
Source dataset
uspto-grants-2010_10
Patent number
US07807690B2

Reaction notes

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