(+-)-3-Phenyllactic acid → HCID 18512718, compound

HRID 1370716Notes

Reaction equation

HRID 1370716 reaction equation
[C:1]1([CH2:7][CH:8]([OH:12])[C:9]([OH:11])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:13]([O:12][CH:8]([CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[C:9]([OH:11])=[O:10])(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 3848(+-)-3-Phenyllactic acidHCID 7412Benzoyl chlorideHCID 8471Triethylamine

Product 1

HCID 18512718HCID 18512718, compoundYield 24.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A 50 mL three-necked flask was charged with 3-phenyllactic acid (1.0 g, 6.0 mmol) and dry CH2Cl2 (12 mL). To this white slurry was added benzoyl chloride (1.04 mL, 9.0 mmol) and the mixture was cooled to 0° C. Triethylamine (0.8 mL, 6.0 mmol) was added and a light yellow solution resulted. 4-Dimethylaminopyridine (367 mg, 3.0 mmol) was added and the reaction mixture was warmed to 25° C. and stirred for 3 hours. The reaction mixture was concentrated on a rotary evaporator and ether, ethyl acetate, and water were added. The mixture was extracted with ether (3×) and ethyl acetate, dried over MgSO4, filtered and evaporated. Purification by silica gel chromatography (4:1 hexanes/ethyl acetate increased to 1:1 hexanes/ethyl acetate) yielded 392 mg (24%) of 11 as a white solid. Rf 0.15 (1:1 hexanes/ethyl acetate); mp 113° C.; IR (CDCl3) 3564-2560 (broad acid), 3028, 2924, 1720 (broad), 1452, 1268, 716 cm−1; 1H NMR (300 MHz, CDCl3) 11.25 (s, 1H), 8.08 (d, J=7.2 Hz, 2H) 7.45 (m, 8H), 5.56 (m, 1H), 3.38 (m, 2H); 13C NMR (75 MHz, CDCl3) 175.5, 165.9, 149.9, 135.6, 133.4, 130.1, 129.7, 129.3, 128.9, 128.5, 128.4, 127.1, 72.9, 37.2; HRMS (FAB): Calcd for (M+Li) C16H14O4Li, 277.1052; Found, 277.1065; EA Calcd for C16H14O4: C, 71.10; H, 5.22; Found: C, 71.04; H, 5.24.

Workup

  1. customa light yellow solution resulted
  2. temperaturethe reaction mixture was warmed to 25° C.
  3. concentrationThe reaction mixture was concentrated on a rotary evaporator and ether, ethyl acetate, and water
  4. additionwere added
  5. extractionThe mixture was extracted with ether (3×) and ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customPurification
  10. temperatureby silica gel chromatography (4:1 hexanes/ethyl acetate increased to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-9cd6337696854f07a7379dfa1de546e6
Source dataset
uspto-grants-2003_06
Patent number
US06583292B2

Reaction notes

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