Triphenylphosphine → HCID 22671278, compound

HRID 1097343Notes

Reaction equation

HRID 1097343 reaction equation
[CH:1]([O:4]C(N=NC(OC(C)C)=O)=O)(C)[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:34][C:35]1[CH:45]=[C:44]([CH2:46]O)[CH:43]=[CH:42][C:36]=1[O:37][CH2:38][C:39]([NH2:41])=[O:40].[S:48]1C=CC=C1CC(O)=O>C1COCC1>[C:1]([S:48][CH2:46][C:44]1[CH:43]=[CH:42][C:36]([O:37][CH2:38][C:39]([NH2:41])=[O:40])=[C:35]([Cl:34])[CH:45]=1)(=[O:4])[CH3:2]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 159702-Thiopheneacetic acidHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22671343HCID 22671343, compound

Product 1

HCID 22671278HCID 22671278, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Diisopropylazocarboxylate (5.5 ml) was added to a stirred solution of triphenylphosphine (7.31 g) in THF at 0° C. Upon completion of addition a colourless precipitate deposited. To this suspension was added a mixture of the product from example 15 step b) (3.0 g) and thiolacetic acid (2.00 ml) in THF (30 ml) at 0° C. The mixture was allowed to attain room temp overnight, evaporated to dryness and the residue purified (SiO2, 10% ethyl acetate: 90% ether as eluant) to give the subtitle compound (3.5 g).

Workup

  1. additionUpon completion of addition a colourless precipitate
  2. additionTo this suspension was added
  3. customevaporated to dryness
  4. customthe residue purified (SiO2, 10% ethyl acetate: 90% ether as eluant)

Sources & evidence

ORD record
ord-59e9f35ecb3b4c4b965b972b4f4ab854
Source dataset
uspto-grants-2012_03
Patent number
US08143261B2

Reaction notes

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