Triphenylphosphine → HCID 23157636, compound

HRID 508112Notes

Reaction equation

HRID 508112 reaction equation
O[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([NH:26][C:27](=[O:29])[CH3:28])=[C:7]([C:9]2[C:14]([CH3:15])=[CH:13][C:12]([O:16][CH2:17][C:18]3([OH:24])[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)=[CH:11][C:10]=2[CH3:25])[CH:8]=1.[F:30][C:31]1[CH:36]=[C:35]([NH:37][S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N+:47]([O-:49])=[O:48])(=[O:40])=[O:39])[CH:34]=[CH:33][C:32]=1[CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:27]([NH:26][C:6]1[C:7]([C:9]2[C:10]([CH3:25])=[CH:11][C:12]([O:16][CH2:17][C:18]3([OH:24])[CH2:23][CH2:22][S:21][CH2:20][CH2:19]3)=[CH:13][C:14]=2[CH3:15])=[CH:8][C:3]([CH2:2][N:37]([S:38]([C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=2[N+:47]([O-:49])=[O:48])(=[O:39])=[O:40])[C:35]2[CH:34]=[CH:33][C:32]([CH2:50][CH2:51][C:52]([O:54][CH2:55][CH3:56])=[O:53])=[C:31]([F:30])[CH:36]=2)=[CH:4][CH:5]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23157368Ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoateHCID 23157518HCID 23157518, compound

Product 1

HCID 23157636HCID 23157636, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-{5-(hydroxymethyl)-4′-[(4-hydroxytetrahydro-2H-thiopyran-4-yl)methoxy]-2′,6′-dimethylbiphenyl-2-yl}acetamide (148 mg, 0.36 mmol), ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (157 mg, 0.40 mmol) and triphenylphosphine (189 mg, 0.72 mmol) in tetrahydrofuran (4 mL) was added diethyl azodicarboxylate (40% toluene solution, 0.33 mL, 0.72 mmol) under stirring at room temperature, and the mixture was stirred for one day. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/3) to give the title compound (262 mg, yield 83%) as a colorless amorphous powder.

Workup

  1. stirringthe mixture was stirred for one day
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=9/1-hexane/ethyl acetate=1/3)

Sources & evidence

ORD record
ord-2d1498903a864e54aa0944470d92d861
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…