Gamma-Aminobutyric Acid → HCID 86613534, compound

HRID 2237736Notes

Reaction equation

HRID 2237736 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][C@H:8]([CH:22]([CH3:24])[CH3:23])[CH2:9][C@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[C@@H:11]2[CH2:13][O:12]2)=[CH:5][C:4]=1[O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32].[NH2:33][CH2:34][CH2:35][CH2:36][C:37]([OH:39])=O.[OH-].[Na+].Cl>C(O)(C)C>[OH:12][C@H:11]([C@@H:10]([NH:14][C:15](=[O:21])[O:16][C:17]([CH3:19])([CH3:20])[CH3:18])[CH2:9][C@H:8]([CH2:7][C:6]1[CH:25]=[CH:26][C:3]([O:2][CH3:1])=[C:4]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:5]=1)[CH:22]([CH3:23])[CH3:24])[CH2:13][N:33]1[CH2:34][CH2:35][CH2:36][C:37]1=[O:39]

Participants

6

Reactant 4

HCID 119Gamma-Aminobutyric AcidHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59849018HCID 59849018, compound

Product 1

HCID 86613534HCID 86613534, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 0.025 g of tert-butyl {3(S)-[4-methoxy-3-(3-methoxypropoxy)benzyl]-4-methyl-1(S)-(R)-oxiranylpentyl}carbamate (Example 1b) in 0.50 ml of isopropanol is admixed successively with 0.027 g of 4-aminobutyric acid and 0.13 ml of 1M NaOH and stirred at 60° C. over 3 hours. The reaction mixture is cooled to 0° C. and admixed with 0.13 ml of 1M HCl and concentrated by evaporation to dryness. The residue is dissolved in 2.5 ml of dichloromethane, admixed successively with 0.016 g of N,N-dicyclohexylcarbodiimide and 0.012 mg of 1-hydroxybenzotriazole, and stirred at room temperature over 18 hours. The reaction solution is admixed with 1M sodium hydrogen carbonate solution and extracted with ethyl acetate (2×). The combined organic phases are washed with brine, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a colourless oil. Rf=0.32 (200:20:1 dichloromethane-methanol-25% conc. ammonia); Rt=4.51 (gradient I).

Workup

  1. temperatureThe reaction mixture is cooled to 0° C.
  2. concentrationconcentrated by evaporation to dryness
  3. dissolutionThe residue is dissolved in 2.5 ml of dichloromethane
  4. stirringstirred at room temperature over 18 hours
  5. extractionextracted with ethyl acetate (2×)
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-2ac7bf3b3e474d86a0f1ab468010f9a5
Source dataset
uspto-grants-2010_05
Patent number
US07718675B2

Reaction notes

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