tert-Butanol → HCID 68540442, compound

HRID 1993682Notes

Reaction equation

HRID 1993682 reaction equation
[C:1]1([CH3:19])[CH:6]=[CH:5][C:4]([N:7]2[C:11](C(O)=O)=[CH:10][C:9]([Si:15]([CH3:18])([CH3:17])[CH3:16])=[N:8]2)=[CH:3][CH:2]=1.C([N:22]([CH2:25]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:34])C=CC=CC=1.[C:44]([OH:48])([CH3:47])([CH3:46])[CH3:45]>C1(C)C=CC=CC=1>[C:44]([O:48][C:25](=[O:34])[NH:22][C:11]1[N:7]([C:4]2[CH:3]=[CH:2][C:1]([CH3:19])=[CH:6][CH:5]=2)[N:8]=[C:9]([Si:15]([CH3:16])([CH3:17])[CH3:18])[CH:10]=1)([CH3:47])([CH3:46])[CH3:45]

Participants

6

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 68537893HCID 68537893, compound

Product 1

HCID 68540442HCID 68540442, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

Place 2-p-tolyl-5-trimethylsilanyl-2H-pyrazole-3-carboxylic acid (620 mg, 2.26 mmol) in tert-butanol (5 mL) and toluene (5 mL). Add triethylamine (0.378 mL, 2.71 mmol), followed by diphenyl phosphoryl azide (0.586 mL, 2.71 mmol) and heat to 60° C. for 1 hour. Then heat to 100° C. for 19 hours. Concentrate reaction under reduced pressure. Subject residue to silica gel chromatography eluting with 0-30% EtOAc:hexane to yield 504 mg (65%) of (2-p-tolyl-5-trimethylsilanyl-2H-pyrazol-3-yl)-carbamic acid tert-butyl ester. MS(ES+): m/z=346.4 [M+H].

Workup

  1. temperatureThen heat to 100° C. for 19 hours
  2. concentrationConcentrate
  3. customreaction under reduced pressure
  4. washSubject residue to silica gel chromatography eluting with 0-30% EtOAc

Sources & evidence

ORD record
ord-d5118c4607644fc8abc59cff826f074b
Source dataset
uspto-grants-2010_01
Patent number
US07652015B2

Reaction notes

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