Triphenylphosphine → HCID 86669780, compound

HRID 2371254Notes

Reaction equation

HRID 2371254 reaction equation
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.[C:34]([OH:37])(=[S:36])[CH3:35].[C:38]([C:42]1[CH:47]=[CH:46][C:45]([CH:48]([CH2:66][C:67]2[CH:72]=[CH:71][C:70]([O:73][CH2:74][CH2:75]O)=[CH:69][CH:68]=2)[C:49]([NH:51][C:52]2[CH:57]=[CH:56][C:55]([O:58][CH2:59][CH:60]3[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:54][CH:53]=2)=[O:50])=[CH:44][CH:43]=1)([CH3:41])([CH3:40])[CH3:39]>C1COCC1>[C:38]([C:42]1[CH:43]=[CH:44][C:45]([CH:48]([C:49](=[O:50])[NH:51][C:52]2[CH:53]=[CH:54][C:55]([O:58][CH2:59][CH:60]3[CH2:65][CH2:64][CH2:63][CH2:62][CH2:61]3)=[CH:56][CH:57]=2)[CH2:66][C:67]2[CH:72]=[CH:71][C:70]([O:73][CH2:74][CH2:75][S:36][C:34](=[O:37])[CH3:35])=[CH:69][CH:68]=2)=[CH:46][CH:47]=1)([CH3:39])([CH3:40])[CH3:41]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 67486504HCID 67486504, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 86669780HCID 86669780, compoundYield 75.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of triphenylphosphine (125 mg, 0.48 mmol) in anhydrous THF (5 mL) at 0° C. was added diisopropylazodicarboxylate (94 uL, 0.48 mmol). After stirring for 30 min. a solution consisting of thioacetic acid (34 uL, 0.48 mmol) and 2-(4-tert-Butylphenyl)-N-(4-cyclohexylmethoxyphenyl)-3-[4-(2-hydroxyethoxy)-phenyl]-propionamide (126 mg, 0.23 mmol) was added. The resulting solution was allowed to warm to rt overnight. The mixture was partitioned between ethyl acetate and H2O and the organic portion concentrated under vacuum. Purification of the crude by preparative TLC (SiO2, 2 mm) using hexane/ethyl acetate (4:1) as eluant afforded Thioacetic acid S-(2-{4-[2-(4-tert-Butylphenyl)-2-(4-cyclohexylmethoxyphenyl carbamoyl)-ethyl]-phenoxy}-ethyl)ester (102 mg, 73%). TLC: Rf=0.38 hexane/ethyl acetate (4:1).

Workup

  1. additionwas added
  2. customThe mixture was partitioned between ethyl acetate and H2O
  3. concentrationthe organic portion concentrated under vacuum
  4. customPurification of the crude by preparative TLC (SiO2, 2 mm)

Sources & evidence

ORD record
ord-8b4c8b407ff14775a6104d4a998a702d
Source dataset
uspto-grants-2014_04
Patent number
US08710236B2

Reaction notes

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