Triphenylphosphine → HCID 86700745, compound

HRID 571152Notes

Reaction equation

HRID 571152 reaction equation
[N:1]([C@@H:4]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C@H:5]([OH:24])[CH2:6][N:7]([CH2:19][C:20]([F:23])([CH3:22])[CH3:21])[S:8]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)(=[O:10])=[O:9])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1.O.C(OCC)(=O)C>[NH2:1][C@@H:4]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=1)[C@H:5]([OH:24])[CH2:6][N:7]([CH2:19][C:20]([F:23])([CH3:21])[CH3:22])[S:8]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)(=[O:9])=[O:10]

Participants

5

Reactant 2

HCID 11776TriphenylphosphineHCID 86700746HCID 86700746, compound

Product 1

HCID 86700745HCID 86700745, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

Azide 18f and triphenyl phosphine (1.2 eq) was dissolved in a solution of THF/H2O (4:1). The reaction mixture was allowed to run for 24 h. Upon completion the reaction was diluted with ethyl acetate and extracted 3 times. The organic layers were combined and dried over anhydrous sodium sulfate. The solvent was removed under vacuum and the residue was purified using flash chromatography 60% ethylacetate/hexanes followed by 3% MeOH/CH2Cl2. 55% yield. 1H NMR (400 MHz, Chloroform-d) δ 7.74 (d, J=8.6 Hz, 2H), 7.09 (d, J=8.3 Hz, 2H), 6.98 (d, J=8.5 Hz, 2H), 6.82 (d, J=8.1 Hz, 2H), 3.93-3.90 (m, 1H), 3.85 (s, 3H), 3.77 (s, 3H), 3.51 (dd, J=27.4, 15.1 Hz, 1H), 3.41-3.20 (m, 3H), 3.04-3.01 (m, 1H), 2.88 (d, J=13.7 Hz, 1H), 2.33 (dd, J=13.4, 10.5 Hz, 1H), 1.46 (d, J=21.6 Hz, 3H), 1.37 (d, J=21.4 Hz, 3H).

Workup

  1. extractionextracted 3 times
  2. dry with materialdried over anhydrous sodium sulfate
  3. customThe solvent was removed under vacuum
  4. customthe residue was purified

Sources & evidence

ORD record
ord-bfd48e2947454d879635acd99bda1b5b
Source dataset
uspto-grants-2015_05
Patent number
US09024038B2

Reaction notes

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