Sodium hydride → HCID 68884723, compound

HRID 1294286Notes

Reaction equation

HRID 1294286 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]([CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])[C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:5][CH:4]=1.CS(Cl)(=O)=O.O[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[CH2:42][C:43]([O:45][CH3:46])=[O:44].[H-].[Na+]>C(OCC)(=O)C.O.CN(C)C=O.C(N(CC)CC)C>[C:12]([O:11][C:10]([N:9]([CH2:17][C:18]1[N:19]=[C:20]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[O:21][C:22]=1[CH3:23])[C:6]1[CH:7]=[CH:8][C:3]([CH2:2][O:1][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=2[CH2:42][C:43]([O:45][CH3:46])=[O:44])=[CH:4][CH:5]=1)=[O:16])([CH3:13])([CH3:14])[CH3:15]

Participants

9

Reactant 4

HCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 89719Methyl (2-hydroxyphenyl)acetateHCID 68886047HCID 68886047, compound

Product 1

HCID 68884723HCID 68884723, compoundYield 60%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

To a mixture of t-butyl 4-(hydroxymethyl)phenyl[(5-methyl-2-phenyl-4-oxazolyl)methyl]carbamate (1.0 g), triethylamine (1.01 g) and ethyl acetate (50 mL) was added methanesulfonyl chloride (1.15 g) at 0° C. The reaction mixture was stirred at room temperature for 20 hrs., diluted with ethyl acetate and washed successively with a saturated aqueous sodium hydrogencarbonate and saturated brine. The mixture was dried over anhydrous magnesium sulfate and concentrated to give pale-yellow crystals. To a mixture of the obtained crystals, methyl 2-(2-hydroxyphenyl)acetate (0.55 g) and N,N-dimethylformamide (30 mL) was added sodium hydride (60%, oil, 0.14 g) at 0° C. The mixture was stirred at room temperature for 3 hrs. To the reaction mixture was added water and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water, 2N aqueous sodium hydroxide solution and saturated brine, and dried over anhydrous magnesium sulfate. After concentration of the organic layer, the residue was subjected to silica gel column chromatography to give crystals (0.82 g, 60%) of methyl 2-[2-[4-[(t-butoxycarbonyl)[(5-methyl-2-phenyl-4-oxazolyl)methyl]amino]benzyloxy]phenyl]acetate from a fraction eluted with ethyl acetate-hexane (1:3, v/v). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 85-86° C.

Workup

  1. washwashed successively with a saturated aqueous sodium hydrogencarbonate and saturated brine
  2. dry with materialThe mixture was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated
  4. customto give pale-yellow crystals
  5. stirringThe mixture was stirred at room temperature for 3 hrs
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe organic layer was washed successively with water, 2N aqueous sodium hydroxide solution and saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-52b68fe6dd2746629bfa1610a6da3bf3
Source dataset
uspto-grants-2007_07
Patent number
US07238716B2

Reaction notes

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