Triphenylphosphine → HCID 22711630, compound

HRID 352395Notes

Reaction equation

HRID 352395 reaction equation
O[CH2:2][CH2:3][N:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=1)(=[O:7])=[O:6].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[S:59]1C=CC=C1CC(O)=O>C1COCC1>[SH:59][CH2:2][CH2:3][N:4]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])=[CH:10][CH:9]=1)(=[O:7])=[O:6]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 4465336HCID 4465336, compoundHCID 5363146Diisopropyl azodicarboxylate

Product 1

HCID 22711630HCID 22711630, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Part B: To a solution of 3.0 g (8.2 mmol) of N-(2-hydroxyethyl)-N-(phenylmethyl)-4-(n-butoxy)benzenesulfonamide from Part A and 2.38 g (9.1 mmol) of triphenylphosphine in 40 mL of anhydrous THF at 0 C, was added 1.4 mL (9.1 mmol) of diisopropylazodicarboxylate, followed by 0.65 mL (9.1 mmol) of thiolacetic acid. After stirring at room temperature for 15 hours, the reaction was concentrated and the residue chromatographed on 150 g of silica gel using 20-50% ethyl acetate/hexane to afford 2.4 g of the desired product, which was recrystallized from ethyl acetate/hexane to afford 1.7 g of pure product, m/e=428 (M+Li).

Workup

  1. concentrationthe reaction was concentrated
  2. customthe residue chromatographed on 150 g of silica gel using 20-50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a8c3e32fd421448b8388621975eacb4a
Source dataset
uspto-grants-2004_06
Patent number
US06747027B1

Reaction notes

Loading…