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Formic Acid → 4-[4-(tert-Butoxycarbonyl)phenyl]-2-[4-(methoxycarbonyl)benzyl]butanoic acid

HRID 1913774
Notes
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Reaction equation

HRID 1913774 reaction equation
C(N(CC)CC)C.C(O)=O.[C:11]([O:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([CH2:24][CH2:25][C:26]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)(C(OCC=C)=O)[C:27]([O:29]CC=C)=[O:28])=[CH:20][CH:19]=1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:11]([O:15][C:16]([C:18]1[CH:19]=[CH:20][C:21]([CH2:24][CH2:25][CH:26]([CH2:39][C:40]2[CH:45]=[CH:44][C:43]([C:46]([O:48][CH3:49])=[O:47])=[CH:42][CH:41]=2)[C:27]([OH:29])=[O:28])=[CH:22][CH:23]=1)=[O:17])([CH3:13])([CH3:14])[CH3:12]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 284Formic AcidHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 59180509Diallyl {2-[4-(tert-butoxycarbonyl)phenyl]ethyl}[4-(methoxycarbonyl)benzyl]malonate

Product 1

HCID 591805004-[4-(tert-Butoxycarbonyl)phenyl]-2-[4-(methoxycarbonyl)benzyl]butanoic acidYield 70.2%

Reagents, catalysts & solvents

2
HCID 167845palladium(II) acetateCatalystHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

A solution of 0.79 ml (5.66 mmol) of triethylamine and 0.16 ml (4.29 mmol) of formic acid in 10 ml of dioxane is added to a solution of 920 mg (1.71 mmol) of diallyl {2-[4-(tert-butoxycarbonyl)phenyl]ethyl}[4-(methoxycarbonyl)benzyl]malonate, 31.5 mg (0.12 mmol) of triphenylphosphine and 7.7 mg (0.03 mmol) of palladium acetate in 10 ml of dioxane at room temperature. The reaction mixture is then stirred at 100° C. for 12 hours. After conversion is complete, the reaction solution is cooled and the solvent is removed in vacuo. The resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1). 497 mg (1.2 mmol, 61% yield) of a colourless solid are obtained.

Workup

  1. temperaturethe reaction solution is cooled
  2. customthe solvent is removed in vacuo
  3. customThe resulting residue is purified by flash chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate 4:1→1:1)

Sources & evidence

ORD record
ord-a52f1a2c8080404ba05a72dfe7f94282
Source dataset
uspto-grants-2013_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08609727B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes