Glycine → HCID 57974123, compound

HRID 1367169Notes

Reaction equation

HRID 1367169 reaction equation
[CH3:1][C:2]([CH3:21])([CH2:7][CH2:8][C:9](=O)[C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=1)[C:3]([O:5]C)=O.[NH2:22][CH2:23][C:24]([OH:26])=[O:25].C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[CH3:21][C:2]1([CH3:1])[CH2:7][CH2:8][CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)[N:22]([CH2:23][C:24]([OH:26])=[O:25])[C:3]1=[O:5]

Participants

6

Reactant 3

HCID 750GlycineHCID 5003444Sodium cyanoborohydrideHCID 66973608HCID 66973608, compound

Product 1

HCID 57974123HCID 57974123, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of methyl 2,2-dimethyl-5-oxo-5-[3-(trifluoromethyl)phenyl]pentanoate from Step A (45.0 mg, 0.149 mmol) and glycine (99.0 mg, 1.32 mmol) in MeOH (2 mL) and acetic acid (0.045 mL) was added sodium cyanoborohydride (50.0 mg, 0.794 mmol). The reaction mixture was heated to reflux for 18 h. To the resulting mixture was added xylenes (3 mL) and heated to 140° C. for 4 h. The solvent was removed in vacuo and the crude solid dissolved in DMSO (1 mL). The crude product was purified by HPLC using a reversed phase C18 column and eluting with a gradient of H2O:CH3CN:CF3CO2H—90:10:0.1 to 5:95:0.1. Lyophilization provided the title compound. MS: m/z=330 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 18 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe crude solid dissolved in DMSO (1 mL)
  5. customThe crude product was purified by HPLC
  6. washeluting with a gradient of H2O

Sources & evidence

ORD record
ord-3c1b9752b24742578d571188a5fa57c3
Source dataset
uspto-grants-2011_02
Patent number
US07893079B2

Reaction notes

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