Hydrochloric Acid → Benzyl acetate

HRID 7671

Reaction equation

HRID 7671 reaction equation
C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:12]([O:19][C:20](=[O:23])[CH2:21]N)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CCN(C(C)C)C(C)C.C(OC(NC1C=CC(C(F)(F)F)=CC=1C(O)=O)=O)(C)(C)C.CN([P+](ON1N=NC2C=CC=CC1=2)(N(C)C)N(C)C)C.F[P-](F)(F)(F)(F)F.Cl>CN(C=O)C.CCOC(C)=O>[CH2:12]([O:19][C:20](=[O:23])[CH3:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 6451311O-benzylglycine toluene-p-sulphonateHCID 150338862-((tert-Butoxycarbonyl)amino)-5-(trifluoromethyl)benzoic acid

Product 1

HCID 8785Benzyl acetateYield 215.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Glycine benzyl ester p-toluenesulfonate salt (6.03 g) was dissolved in DMF prior to the addition of Hunig's base (12.4 mL) and 2-(tert-butoxycarbonyl)amino-5-trifluoromethylbenzoic acid (6 g) (Takagishi et al., Synlett 1992, 360). After cooling to 0° C., BOP Reagent (8.69 g) was added. The resulting mixture was warmed to rt and was stirred 96 h. EtOAc was added along with 1 N HCl solution. The EtOAc layer was washed with 1 N HCl (aq), NaHCO3 solution (aq), and brine. The EtOAc was dried (MgSO4), filtered, and concentrated. Flash chromatography of the resulting residue gave 2-tert-butoxycarbonylamino-5-trifluoromethyl-benzoylamino)-acetic acid benzyl ester (5.78 g). MS found: (M+Na)+=475.3.

Workup

  1. temperatureThe resulting mixture was warmed to rt
  2. washThe EtOAc layer was washed with 1 N HCl (aq), NaHCO3 solution (aq), and brine
  3. dry with materialThe EtOAc was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-0224c20f2e144680a90e3f6f2a7fd373
Source dataset
uspto-grants-2006_08
Patent number
US07087604B2

Linked notes

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