tert-Butanol → HCID 13852432, compound

HRID 2351031Notes

Reaction equation

HRID 2351031 reaction equation
[F:1][C@H:2]1[CH2:4][C@H:3]1C(O)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.C([N:27]([CH2:30]C)CC)C.[C:32]([OH:36])([CH3:35])([CH3:34])[CH3:33]>>[C:32]([O:36][C:30]([NH:27][CH:3]1[CH2:4][CH:2]1[F:1])=[O:15])([CH3:35])([CH3:34])[CH3:33]

Participants

5

Reactant 4

HCID 6386tert-ButanolHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 9793716cis-2-Fluorocyclopropanecarboxylic acid

Product 1

HCID 13852432HCID 13852432, compound

Procedure

In 30 ml of tert-butanol was dissolved 2 g of cis-2-fluoro-1-cyclopropanecarboxylic acid. After addition of 8 g of diphenylphosphorylazide (DPPA) and 3 g of triethylamine, the resulting mixture was heated under reflux for 8 hours. After removing the solvent, the residue was subjected to column chromatography using 50 g of silica gel, and 900 mg of 1-tert-butoxycarbonylamino-2-fluorocyclopropane was obtained from chloroform eluate. After allowing to stand, the crystals were washed with n-hexane to yield a sublimatic colorless crystals. m.p. 58°-60° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customAfter removing the solvent

Sources & evidence

ORD record
ord-2c3e3739c211454cae5a35348f903ada
Source dataset
uspto-grants-1989_10
Patent number
US04871852

Reaction notes

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