Triphenylphosphine → HCID 23592304, compound

HRID 1611667Notes

Reaction equation

HRID 1611667 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[NH:9][S:10]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)(=[O:12])=[O:11].[C:20]([O:39][CH2:40][CH2:41][C@@H:42](O)[CH3:43])([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[C:45]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1.CCOC(C)=O>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([S:10]([N:9]([C:3]2[CH:4]=[C:5]([Cl:8])[CH:6]=[CH:7][C:2]=2[Cl:1])[C@H:43]([CH3:45])[CH2:42][CH2:41][CH2:40][O:39][C:20]([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)(=[O:12])=[O:11])=[CH:14][CH:15]=1

Participants

7

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 3101324-chloro-N-(2,5-dichlorophenyl)benzenesulfonamideHCID 13623585HCID 13623585, compound

Product 1

HCID 23592304HCID 23592304, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To N-(2,5-dichlorophenyl)-4-chlorobenzenesulfonamide (5.0 g, 15 mmol), (S) -4-trityloxy-butan-2-ol (7.7 g, 22 mmol), and triphenylphosphine (5.8 g, 22 mmol) in THF (200 mL) at 0° C. was added diethyl azodicarboxylate (3.8 g, 22 mmol). The reaction was allowed to warm to ambient temperature with stirring 18 h The reaction was then diluted with EtOAc and washed with H2O, 1N HCl, and brine. The organic phase was dried over MgSO4, filtered, and concentrated in vacuo. Silica gel chromatography (15% EtOAc/hexanes) of the concentrate afforded the title compound as a white solid (5.25 g, 55% yield).

Workup

  1. washwashed with H2O, 1N HCl, and brine
  2. dry with materialThe organic phase was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-69a21542ecef4b6aac82b1c31822f9e3
Source dataset
uspto-grants-2006_01
Patent number
US06989399B2

Reaction notes

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