Trifluoroacetic acid → 108462-96-0

HRID 2410642Notes

Reaction equation

HRID 2410642 reaction equation
C(OC1C=CC(C(OC2C=CC([CH2:22][CH:23]([NH:31][C:32](=[O:41])[C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[C:24]([O:26]C(C)(C)C)=[O:25])=CC=2OC)=O)=CC=1)CCCCCC.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:40][O:39][C:36]1[CH:35]=[CH:34][C:33]([C:32]([NH:31][CH:23]([CH3:22])[C:24]([OH:26])=[O:25])=[O:41])=[CH:38][CH:37]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68001878HCID 68001878, compound

Product 1

HCID 4067884108462-96-0

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
30 °C

Procedure

A crude solution of 4-(3-(tert-butoxy)-2-(4-methoxybenzamido)-3-oxopropyl)-2-methoxyphenyl 4-(heptyloxy)benzoate in DCM (1 mL) was treated with TFA (0.1 mL) and stirred overnight at 30° C. The solvent was evaporated and the residue was purified by preparative HPLC to give 16.9 mg (48%) of 3-(4-(4-(heptyloxy)benzoyl)oxy)-3-methoxyphenyl)-2-(4-methoxybenzamido)propanoic acid 2. LCMS-ESI (m/z) calculated for C32H37NO8: 563. Found 564 [M+H]+, tR=11.01 min (Method 2). 1H NMR (400 MHz, DMSO) δ 12.79 (s, 1H), 8.57 (d, J=8.1 Hz, 1H), 8.00 (d, J=9.0 Hz, 2H), 7.82 (d, J=8.9 Hz, 2H), 7.13 (d, J=1.7 Hz, 1H), 7.11-7.03 (m, 3H), 6.99 (d, J=8.9 Hz, 2H), 6.92 (dd, J=8.1, 1.7 Hz, 1H), 4.61 (ddd, J=10.8, 8.1, 4.4 Hz, 1H), 4.07 (t, J=6.5 Hz, 2H), 3.80 (s, 3H), 3.69 (s, 3H), 3.20 (dd, J=13.8, 4.2 Hz, 1H), 3.08 (dd, J=13.7, 10.7 Hz, 1H), 1.84-1.66 (m, 2H), 1.51-1.17 (m, 8H), 0.87 (t, J=6.9 Hz, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by preparative HPLC

Sources & evidence

ORD record
ord-eec212750e554619bca7287b14330317
Source dataset
uspto-grants-2014_08
Patent number
US08816121B2

Reaction notes

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