Triphenylphosphine → Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoate

HRID 508090Notes

Reaction equation

HRID 508090 reaction equation
[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15]O)=[CH:11][C:10]=2[CH2:17][CH:18]([CH3:20])[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:27][C:28]1[CH:33]=[C:32]([NH:34][S:35]([C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[N+:44]([O-:46])=[O:45])(=[O:37])=[O:36])[CH:31]=[CH:30][C:29]=1[CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[C:1]1([CH:7]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][N:34]([S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=3[N+:44]([O-:46])=[O:45])(=[O:36])=[O:37])[C:32]3[CH:31]=[CH:30][C:29]([CH2:47][CH2:48][C:49]([O:51][CH2:52][CH3:53])=[O:50])=[C:28]([F:27])[CH:33]=3)=[CH:11][C:10]=2[CH2:17][CH:18]([CH3:20])[CH3:19])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 23157345[4-(Diphenylmethoxy)-3-isobutylphenyl]methanolHCID 23157368Ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate

Product 1

HCID 23157541Ethyl 3-(4-{[4-(diphenylmethoxy)-3-isobutylbenzyl][(2-nitrophenyl)sulfonyl]amino}-2-fluorophenyl)propanoateYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of [4-(diphenylmethoxy)-3-isobutylphenyl]methanol (0.49 g, 1.41 mmol), ethyl 3-(2-fluoro-4-{[(2-nitrophenyl)sulfonyl]amino}phenyl)propanoate (0.62 g, 1.56 mmol) and triphenylphosphine (0.55 g, 2.10 mmol) in tetrahydrofuran (25 mL) was added diethyl azodicarboxylate (40% toluene solution, 0.93 mL, 2.13 mmol) at room temperature, and the mixture was stirred at room temperature for 18 hr. The reaction mixture was concentrated, and the residue was subjected to silica gel column chromatography (ethyl acetate/hexane=3/97-15/85) to give the title compound (800 mg, yield 78%) as a colorless oil.

Workup

  1. concentrationThe reaction mixture was concentrated

Sources & evidence

ORD record
ord-98e604606dae4671a3119bf1527e62f4
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

Loading…