tert-Butanol → HCID 118076294, compound

HRID 1051579Notes

Reaction equation

HRID 1051579 reaction equation
[CH:1]1([O:5][C:6]2[CH:7]=[C:8]([F:16])[C:9]([F:15])=[C:10]([CH:14]=2)C(O)=O)[CH2:4][CH2:3][CH2:2]1.C([N:19]([CH2:22]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:31])C=CC=CC=1.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[CH:1]1([O:5][C:6]2[CH:7]=[C:8]([F:16])[C:9]([F:15])=[C:10]([NH:19][C:22](=[O:31])[O:45][C:41]([CH3:44])([CH3:43])[CH3:42])[CH:14]=2)[CH2:2][CH2:3][CH2:4]1

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 118076076HCID 118076076, compound

Product 1

HCID 118076294HCID 118076294, compoundYield 76%

Procedure

A solution of 5-cyclobutoxy-2,3-difluorobenzoic acid (38 g, 148 mmol), t-butanol (280 mL), triethylamine (21.4 mL, 154 mmol) and diphenylphosphoryl azide (33.2 mL, 154 mmol) stirred overnight at 90° C. The reaction mixture was cooled to room temperature and concentrated. The residue was dissolved dichloromethane (200 mL), washed with 1 M sodium hydroxide (2×100 mL) and brine (2×50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was purified via column chromatography on silica gel (eluting with 5% ethyl acetate/petroleum ether) to afford tert-butyl 5-cyclobutoxy-2,3-difluorophenylcarbamate (32 g, 76%) as a white solid. MS (ESI, pos. ion) m/z 230 [M+H]+.

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved dichloromethane (200 mL)
  3. washwashed with 1 M sodium hydroxide (2×100 mL) and brine (2×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified via column chromatography on silica gel (eluting with 5% ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-a06ed21d92ce4f9bb18782ec38796aae
Source dataset
uspto-grants-2016_07
Patent number
US09388161B2

Reaction notes

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