Water → HCID 72485097, compound

HRID 2267642Notes

Reaction equation

HRID 2267642 reaction equation
[N:1]([CH:4]([CH:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O>C1COCC1>[NH2:1][CH:4]([CH:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=1[N+:25]([O-:27])=[O:26])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 11776TriphenylphosphineHCID 72485110HCID 72485110, compound

Product 1

HCID 72485097HCID 72485097, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl (2SR,3RS)-2-azido-3-(4-fluoro-2-nitrophenoxy)-3-phenylpropanoate (b) (2.60 g) and triphenylphosphine (2.01 g) in THF (100 ml) was added water (2 ml) and the mixture was refluxed for 1 h then stirred at RT overnight. The reaction was concentrated in vacuo and the resulting residue was purified by flash chromatography (5:2 hexane:ethyl acetate) to afford the title compound (1.55 g) as a yellow oil. 1H NMR (300 MHz, d6-DMSO) δ 1.01 (t, 3H, J=7 Hz), 1.85 (s, 2H), 3.76 (d, 1H, J=5 Hz), 3.99 (q, 2H, J=7 Hz), 5.75 (d, 1H, J=5 Hz), 6.89-7.44 (m, 7H), 7.85 (dd, 1H, J=3 Hz, J=9 Hz). MS APCI, m/z=349 (M+1). LC/MS: 1.82 min.

Workup

  1. temperaturethe mixture was refluxed for 1 h
  2. concentrationThe reaction was concentrated in vacuo
  3. customthe resulting residue was purified by flash chromatography (5:2 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-0785499637c94401ba5167cc1af783ab
Source dataset
uspto-grants-2010_12
Patent number
US07858776B2

Reaction notes

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