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Triphenylphosphine → Diphenylmethyl 2-acetylthio-3-(4-fluorophenyl)propionate

HRID 1489558
Notes
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Reaction equation

HRID 1489558 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[C:34]([OH:37])(=[S:36])[CH3:35].[F:38][C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH:46](O)[C:47]([O:49][CH:50]([C:57]2[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=2)[C:51]2[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=2)=[O:48])=[CH:41][CH:40]=1>O1CCCC1>[C:34]([S:36][CH:46]([CH2:45][C:42]1[CH:43]=[CH:44][C:39]([F:38])=[CH:40][CH:41]=1)[C:47]([O:49][CH:50]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)[C:57]1[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=1)=[O:48])(=[O:37])[CH3:35]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 22902076Diphenylmethyl 3-(4-fluorophenyl)lactateHCID 178418634HCID 178418634, compound

Product 1

HCID 22902069Diphenylmethyl 2-acetylthio-3-(4-fluorophenyl)propionateYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Triphenylphosphine (3.99 g, 15.2 mmol) was dissolved in dry tetrahydrofuran (78 ml), followed by cooling to 0° C. under cooling with ice. Further, diisopropyl azodicarboxylate (DIAD (2.99 ml, 15.2 mmol)) was dropped thereinto under stirring. Thirty minutes thereafter, a solution of a mixture of thioacetic acid (1.25 ml, 17.8 mmol) with diphenylmethyl 3-(4-fluorophenyl)lactate (4.0 g, 11.4 mmol) obtained in the Synthesis Example F-1 in dry tetrahydrofuran (45 ml) was dropped thereinto. The mixture was allowed to react at 0° C. for 3 hours. Then the ice bath was removed and the reaction mixture was warmed to room temperature and allowed to react at this temperature overnight. Next, this reaction mixture was concentrated under reduced pressure. The residue thus obtained was separated by silica gel column chromatography (hexane:ethyl acetate=6:1) to thereby give a crude product (4.7 g). This crude product was recrystallized from diisopropyl ether and hexane (20 ml-30 ml). The solid thus precipitated was removed by filtration and the filtrate was concentrated under reduced pressure to thereby give the title compound (3.54 g, 76%) as an oily product.

Workup

  1. temperatureunder cooling with ice
  2. additionwas dropped
  3. customto react at 0° C. for 3 hours
  4. customThen the ice bath was removed
  5. temperaturethe reaction mixture was warmed to room temperature
  6. customto react at this temperature overnight
  7. concentrationNext, this reaction mixture was concentrated under reduced pressure
  8. customThe residue thus obtained
  9. customwas separated by silica gel column chromatography (hexane:ethyl acetate=6:1)
  10. customto thereby give a crude product (4.7 g)
  11. customThis crude product was recrystallized from diisopropyl ether and hexane (20 ml-30 ml)
  12. customThe solid thus precipitated
  13. customwas removed by filtration
  14. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-de54377352ac41ecbaef01a07474d177
Source dataset
uspto-grants-1997_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05679671

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes