tert-Butanol → HCID 90203276, compound

HRID 927037Notes

Reaction equation

[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:13](C(O)=O)=[CH:12][O:11][N:10]=2)=[CH:5][CH:4]=1)#[N:2].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:24])C=CC=CC=1.C([N:36]([CH2:39]C)CC)C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[C:41]([O:45][C:39](=[O:24])[NH:36][C:13]1[C:9]([C:6]2[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:8][CH:7]=2)=[N:10][O:11][CH:12]=1)([CH3:44])([CH3:43])[CH3:42]

Participants

Reactant 4

HCID 6386tert-Butanol

HCID 8471Triethylamine

HCID 199401P,P-Diphenylphosphinic azide

HCID 90203448HCID 90203448, compound

Product 1

HCID 90203276HCID 90203276, compoundYield 33%

Conditions

Temperature: 80 °C

Procedure

A solution of 3-(4-cyano-phenyl)-isoxazole-4-carboxylic acid (4.7 g, 22 mmol) in tert-butanol was treated with diphenylphosphoryl azide (5.1 mL, 24 mmol) and triethylamine (3.33 mL, 24 mmol). The solution was heated to 80° C. for 14 h and then all volatiles were removed under reduced pressure to give [3-(4-cyano-phenyl)-isoxazol-4-yl]-carbamic acid tert-butyl ester (2.1 g, 33%).

Workup

customall volatiles were removed under reduced pressure

Sources & evidence

ORD record: ord-65f0105e14ee4005a24181f451e977a7
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290465B2

Reaction notes

Loading…