tert-Butanol → HCID 68779984, compound

HRID 2264136Notes

Reaction equation

HRID 2264136 reaction equation
[F:1][C:2]1[C:11](C([O-])=O)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CC[N:17]([CH2:20]C)CC.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:29])C=CC=CC=1.[C:39]([OH:43])([CH3:42])([CH3:41])[CH3:40]>>[C:39]([O:43][C:20]([NH:17][C:11]1[C:2]([F:1])=[C:3]([CH:8]=[CH:9][CH:10]=1)[C:4]([O:6][CH3:7])=[O:5])=[O:29])([CH3:42])([CH3:41])[CH3:40]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 86313868HCID 86313868, compound

Product 1

HCID 68779984HCID 68779984, compound

Procedure

A solution of monomethyl 2-fluoroisophthalate (0.4 g) in tert-butyl alcohol (10 mL) was treated with Et3N (0.56 mL) and diphenylphosphoryl azide (0.75 mL). After 1 h, the mixture was heated at reflux for 24 h, then cooled and concentrated. The residue was diluted with EtOAc, washed with saturated aqueous NaHCO3, dried over MgSO4, filtered, and evaporated. Silica gel chromatography (acetone/hexane gradient) provided the product. 1H-NMR (CDCl3): δ 8.31 (1H, br t, J=7.2 Hz), 7.55 (1H, ddd, J=1.6, 6.8, 8.0 Hz), 7.16 (1H, ddd, J=1.2, 8.0, 8.0 Hz), 6.80 (1H, br s), 3.93 (3H, s), 1.54 (9H, s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 24 h
  3. temperaturecooled
  4. concentrationconcentrated
  5. additionThe residue was diluted with EtOAc
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. customevaporated
  10. customSilica gel chromatography (acetone/hexane gradient) provided the product

Sources & evidence

ORD record
ord-7b5c3f7b520a4cfdb91ff30bdb1f4056
Source dataset
uspto-grants-2010_12
Patent number
US07855192B2

Reaction notes

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