Water → HCID 76071552, compound

HRID 927034Notes

Reaction equation

HRID 927034 reaction equation
[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:19](C(O)=O)=[CH:18][O:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.C([N:27](CC)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.O>CN(C=O)C.CCCCCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:19]([NH2:27])=[CH:18][O:17][N:16]=3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 90203857HCID 90203857, compound

Product 1

HCID 76071552HCID 76071552, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
52.5 °C

Procedure

A solution of 3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazole-4-carboxylic acid (1.0 g, 3.07 mmol) and triethylamine (0.5 mL, 3.4 mmol) in DMF (30 mL) was cooled to 0° C. Diphenylphosphorylazide (0.8 mL, 3.86 mmol) was added and the reaction mixture was warmed to 45-60° C. for 2 h. Water (15 mL) was then added and the reaction temperature increased to 90° C. for 28 h. The reaction mixture was cooled and 3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazol-4-ylamine was isolated by chromatography (5-40% ethyl acetate in hexane) as a white solid. m.p. 92-98° C. HRMS+1=297.123

Workup

  1. temperaturethe reaction temperature increased to 90° C. for 28 h
  2. temperatureThe reaction mixture was cooled

Sources & evidence

ORD record
ord-eaff85ccad73471b8b7cd04727d5d0d9
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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