Triphenylphosphine → HCID 18779213, compound

HRID 1422312Notes

Reaction equation

HRID 1422312 reaction equation
[C:1]1([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:8]2[CH:12]=[C:11]([CH2:13][CH2:14][CH2:15][CH2:16]O)[N:10]=[CH:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:30]([O:34][C:35]([NH:37][S:38]([NH:41][CH2:42][CH:43]1[CH2:48][CH2:47][CH2:46][CH2:45][CH2:44]1)(=[O:40])=[O:39])=[O:36])([CH3:33])([CH3:32])[CH3:31].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O>O1CCCC1>[C:30]([O:34][C:35]([N:37]([CH2:16][CH2:15][CH2:14][CH2:13][C:11]1[N:10]=[CH:9][N:8]([C:7]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=1)[S:38]([NH:41][CH2:42][CH:43]1[CH2:44][CH2:45][CH2:46][CH2:47][CH2:48]1)(=[O:40])=[O:39])=[O:36])([CH3:33])([CH3:31])[CH3:32]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 11596091HCID 11596091, compoundHCID 18779221HCID 18779221, compound

Product 1

HCID 18779213HCID 18779213, compoundYield 60.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product from step d (764 mg, 2.00 mmol), the product from step e (642 mg, 2.20 mmol) and triphenylphosphine 576 mg, 2.20 mmol) in dry tetrahydrofuran (20 ml), under an atmosphere of argon, was added over 10 min a solution of diethylazodicarboxylate (383 mg, 2.20 mmol) in dry tetrahydrofuran (5 ml). The mixture was stirred for 2 h, the solvent evaporated and the residue purified by flash column chromatography (silica; 30% ethyl acetate/dichloromethane). Thus, the product was isolated as a colourless foam (800 mg, 60%).

Workup

  1. customthe solvent evaporated
  2. customthe residue purified by flash column chromatography (silica; 30% ethyl acetate/dichloromethane)

Sources & evidence

ORD record
ord-d95920cbdad941c09783c85b476cc576
Source dataset
uspto-grants-2000_06
Patent number
US06080871

Reaction notes

Loading…