Triethylamine → HCID 70105059, compound

HRID 2305238Notes

Reaction equation

HRID 2305238 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([C:18]3[CH:19]([CH2:24][C:25]4[CH:26]=[C:27]([CH:31]=[CH:32][CH:33]=4)C(O)=O)[CH2:20][CH2:21][CH2:22][CH:23]=3)[O:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([N:36]([CH2:39]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:48])C=CC=CC=1.[C:58]([OH:62])([CH3:61])([CH3:60])[CH3:59].C1(C)C=CC=CC=1>>[C:58]([O:62][C:39](=[O:48])[NH:36][C:27]1[CH:31]=[CH:32][CH:33]=[C:25]([CH2:24][CH:19]2[CH2:20][CH2:21][CH2:22][CH:23]=[C:18]2[C:9]2[O:10][C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[N:8]=2)[CH:26]=1)([CH3:61])([CH3:60])[CH3:59]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 98458443-{(2-(4,5-Diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoic acidHCID 22595558Toluene tert-butyl alcohol

Product 1

HCID 70105059HCID 70105059, compoundYield 78%

Conditions

Temperature
80 °C

Procedure

A mixture of 3-{(2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}benzoic acid (2.60 g, 5.98 mmol), triethylamine (1.08 ml, 7.77 mmol), and diphenylphosphoryl azide (1.67 ml, 7.77 mmol) in t-butanol-toluene (2:1, 80 ml) was stirred at 80° C. for 18 hours. After cooling the mixture to room temperature, the mixture was evaporated, diluted with EtOAc, washed with saturated sodium hydrogencarbonate solution, water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:EtOAc, 8:1 elution) to give {3-{[2-(4,5-diphenyloxazol-2-yl)-2-cyclohexen-1-yl]methyl}phenyl}carbamic acid tert-butyl ester (2.36 g, 78%).

Workup

  1. temperatureAfter cooling the mixture to room temperature
  2. customthe mixture was evaporated
  3. additiondiluted with EtOAc
  4. washwashed with saturated sodium hydrogencarbonate solution, water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane:EtOAc, 8:1 elution)

Sources & evidence

ORD record
ord-514508fea2274155ad73694aaf562c3f
Source dataset
uspto-grants-2002_08
Patent number
US06437146B1

Reaction notes

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