tert-Butanol → HCID 14278962, compound

HRID 868158Notes

Reaction equation

HRID 868158 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[CH:13][N:12]=[C:11](C(O)=O)[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.C([N:45]([CH2:48]C)CC)C.[C:50]([OH:54])([CH3:53])([CH3:52])[CH3:51]>>[C:1]1([CH2:7][O:8][C:9]2[C:14]([O:15][CH2:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)=[CH:13][N:12]=[C:11]([NH:45][C:48](=[O:33])[O:54][C:50]([CH3:53])([CH3:52])[CH3:51])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 141825074,5-bis(phenylmethoxy)-2-Pyridinecarboxylic acid

Product 1

HCID 14278962HCID 14278962, compound

Conditions

Temperature
80 °C

Procedure

To a suspension of 1.5 g (4.5 mmol) of 4,5-bis(phenylmethoxy)-2-pyridinecarboxylic acid in 25 ml of t-butanol were added 1.5 g (5.4 mmol) of diphenylphosphoryl azide and 0.54 g (5.4 mmol) of triethylamine. The mixture was stirred at 80° C. for 17 hours. After cooling to room temperature, the crystals were filtered off, washed with ether and dried in vacuo. Yield: 1.3 g. Concentration of the mother liquor yielded another 0.3 g of product. Total yield: 1.6 g; melting point 163.3° C.

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe crystals were filtered off
  3. washwashed with ether
  4. customdried in vacuo

Sources & evidence

ORD record
ord-2d097605f9f2456b90271ee7f607ad5f
Source dataset
uspto-grants-1988_10
Patent number
US04777252

Reaction notes

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