tert-Butanol → HCID 90203445, compound

HRID 927029Notes

Reaction equation

HRID 927029 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.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:32])C=CC=CC=1.C([N:44]([CH2:47]C)CC)C.[C:49]([OH:53])([CH3:52])([CH3:51])[CH3:50]>CN(C=O)C>[C:49]([O:53][C:47](=[O:32])[NH:44][C:19]1[C:15]([C:12]2[CH:11]=[CH:10][C:9]([O:8][CH2:7][C:6]3[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:24][CH:23]=3)=[CH:14][CH:13]=2)=[N:16][O:17][CH:18]=1)([CH3:52])([CH3:51])[CH3:50]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 90203857HCID 90203857, compound

Product 1

HCID 90203445HCID 90203445, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazole-4-carboxylic acid (16.16 g, 49.7 mmol) in DMF (50 mL) was added diphenylphosphoryl azide (15.04 g, 54.6 mmol) and triethylamine (7.62 mL, 54.64 mmol). The orange solution was heated to 50° C. and allowed to stir 3.5 h. At this time, tert-butanol (100 mL) was added and the reaction mixture was heated to 84° C. for 14 h after which it was cooled to rt. Concentration in vacuo gave a dark orange oil from which {3-[4-(4-methoxy-benzyloxy)-phenyl]-isoxazol-4-yl}-carbamic acid tert-butyl ester (3.01 g, 15%) was isolated by chromatography (25-50% ethyl acetate in hexane).

Workup

  1. temperaturethe reaction mixture was heated to 84° C. for 14 h after which it
  2. temperaturewas cooled to rt
  3. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-605f11f0693d46eca9bf7a3f28346dd8
Source dataset
uspto-grants-2016_03
Patent number
US09290465B2

Reaction notes

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