Trifluoroacetic acid → 2-(Diethoxy-phosphoryl)-4-phenyl-butyric acid

HRID 902938Notes

Reaction equation

HRID 902938 reaction equation
FC(F)(F)C(O)=O.C([O:12][C:13](=[O:31])[CH:14]([P:23]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])=[O:24])[CH2:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)(C)(C)C>ClCCl>[CH2:29]([O:28][P:23]([CH:14]([CH2:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:13]([OH:31])=[O:12])([O:25][CH2:26][CH3:27])=[O:24])[CH3:30]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 865943852-(Diethoxy-phosphoryl)-4-phenyl-butyric acid tert-butyl ester

Product 1

HCID 219570062-(Diethoxy-phosphoryl)-4-phenyl-butyric acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (4 mL) was added drop wise to a stirring solution of 2-(diethoxy-phosphoryl)-4-phenyl-butyric acid tert-butyl ester (1.00 g, 2.81 mmol) in anhydrous dichloromethane (16 ml). The mixture was stirred for 2 hours at room temperature followed by the removal of the solvent. The crude residue was purified by flash chromatography (100% dichloromethane-2.5% methanol in dichloromethane) to afford the desired compound as a yellowish oil. 1H NMR (CDCl3, 400 MHz) δ 11.21 (br s, 1H), 7.29-7.14 (m, 5H), 4.24-4.12 (m, 4H), 3.09-3.00 (m, 1H), 2.82-2.75 (m, 1H), 2.64-2.57 (m, 1H), 2.35-2.27 (m, 1H), 2.15-2.11 (m, 1H), 1.31-1.25 (m, 6H); 13C (CDCl3, 100 MHz) δ 170.4, 140.4, 128.4, 128.3, 126.1, 63.4, 63.2, 45.1, 43.8, 34.0, 28.5, 16.0; 31P (CDCl3, 400 MHz) δ 24.3; HRMS calcd. for C14H21O5P 300.1127, found 300.1129.

Workup

  1. customfollowed by the removal of the solvent
  2. customThe crude residue was purified by flash chromatography (100% dichloromethane-2.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-7cbadb66f8af42ec94ee881c3ef4703d
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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