Triphenylphosphine → HCID 71696612, compound

HRID 1485837Notes

Reaction equation

HRID 1485837 reaction equation
[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([OH:15])[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[F:35][C:36]1[CH:37]=[C:38]([C:42]2[CH:47]=[C:46](O)[CH:45]=[CH:44][C:43]=2[CH2:49][CH2:50][NH:51][C:52](=[O:54])[CH3:53])[CH:39]=[CH:40][CH:41]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.C([O-])(O)=O.[Na+]>C1COCC1>[CH2:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([O:15][C:46]2[CH:45]=[CH:44][C:43]([CH2:49][CH2:50][NH:51][C:52](=[O:54])[CH3:53])=[C:42]([C:38]3[CH:39]=[CH:40][CH:41]=[C:36]([F:35])[CH:37]=3)[CH:47]=2)[CH:11]=[CH:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 11776TriphenylphosphineHCID 516892Sodium BicarbonateHCID 5363146Diisopropyl azodicarboxylateHCID 12827154HCID 12827154, compoundHCID 89752224HCID 89752224, compound

Product 1

HCID 71696612HCID 71696612, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 35 (70 mg, 0.34 mmol) in freshly distilled THF (3 mL) at 0° C. was added triphenyl phosphine (180 mg, 0.68 mmol) and 23 (90 mg, 0.34 mmol). DIAD (0.135 mL, 0.68 mmol) was added to the mixture dropwise. The reaction was warmed to room temperature and stirred for 4 h. The reaction mixture was treated with saturated aqueous NaHCO3 solution (2 mL), washed with water, followed by brine, dried over Na2SO4, and concentrated to give a crude mixture that was purified by column chromatography (30% 50% EtOAc in hexane) to give 36 as an oil.

Workup

  1. washwashed with water
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customto give a crude mixture that
  5. customwas purified by column chromatography (30% 50% EtOAc in hexane)

Sources & evidence

ORD record
ord-66c20475096647fa82d23ebe22ab772a
Source dataset
uspto-grants-2016_08
Patent number
US09422320B2

Reaction notes

Loading…