Trifluoroacetic acid → 2-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-hydroxy-5-(4-iodophenyl)pentanoic acid

HRID 1818875Notes

Reaction equation

HRID 1818875 reaction equation
FC(F)(F)C(O)=O.[O:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]1[CH2:19][CH2:20][CH:21]([CH:29]([O:39]CC1C=CC(OC)=CC=1)[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([I:38])=[CH:34][CH:33]=1)[C:22]([O:24]C(C)(C)C)=[O:23]>ClCCl>[O:8]=[C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:11](=[O:18])[N:10]1[CH2:19][CH2:20][CH:21]([CH:29]([OH:39])[CH2:30][CH2:31][C:32]1[CH:37]=[CH:36][C:35]([I:38])=[CH:34][CH:33]=1)[C:22]([OH:24])=[O:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 578870191,1-Dimethylethyl 2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(4-iodophenyl)-3-({[4-(methyloxy)phenyl]methyl}oxy)pentanoate

Product 1

HCID 578870292-[2-(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-3-hydroxy-5-(4-iodophenyl)pentanoic acidYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (5 mL) was added in one portion to a stirred solution of 1,1-dimethylethyl 2-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]-5-(4-iodophenyl)-3-({[4-(methyloxy)phenyl]methyl}oxy)pentanoate (261 mg, 0.390 mmol) in dichloromethane (5 mL) at room temperature under nitrogen. The resulting solution was stirred for 45 min then the volatiles evaporated to give the title compound (192 mg, 100%) as a yellow solid which was a mixture of diastereomers. LC/MS: 3.32 min; z/e 493, calcd (M+1) 493. 1H NMR (400 MHz: CDCl3): 7.85 (4H), 7.55 (2H), 6.95 (2H), 4.90 (1H), 3.80-3.50 (3H), 2.70-2.20 (3H), 1.85 (2H), 1.55 (2H).

Workup

  1. customthe volatiles evaporated

Sources & evidence

ORD record
ord-c7233e0135894ba49a8d26fdb469a011
Source dataset
uspto-grants-2009_10
Patent number
US07601729B2

Reaction notes

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