Hydrochloric Acid → HCID 118292778, compound

HRID 1486909Notes

Reaction equation

HRID 1486909 reaction equation
[C:1]([O:5][C:6](=[O:33])[CH2:7][C:8]1([CH2:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[O:12][N:11]=[C:10]([C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=2[CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].Br[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.C(N(CC)C(C)C)(C)C.Cl>CN(C=O)C>[C:28]([O:27][C:26](=[O:32])[CH2:25][C:8]1([CH2:7][C:6](=[O:33])[O:5][C:1]([CH3:3])([CH3:2])[CH3:4])[O:12][N:11]=[C:10]([C:13]2[CH:18]=[C:17]([OH:19])[CH:16]=[CH:15][C:14]=2[CH2:20][CH2:21][C:22]([O:24][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:23])[CH2:9]1)([CH3:31])([CH3:30])[CH3:29]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 118292738HCID 118292738, compound

Product 1

HCID 118292778HCID 118292778, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 3-(2-(5,5-bis(2-tert-butoxy-2-oxoethyl)-4,5-dihydro-1,2-oxazol-3-yl)-4-hydroxyphenyl)propanoic acid (413 mg), (bromomethyl)benzene (0.117 mL), N,N-diisopropylethylamine (0.342 mL), and DMF (4 mL) was stirred overnight at room temperature. To the reaction mixture, 0.1 M hydrochloric acid was added, followed by extraction with ethyl acetate. The extract was washed with brine and dried over anhydrous magnesium sulfate, and then, the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to obtain the title compound (227 mg).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-6171840de0eb45858065a200b2cac45c
Source dataset
uspto-grants-2016_08
Patent number
US09428470B2

Reaction notes

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