Gamma-Aminobutyric Acid → HCID 67145507, compound

HRID 1425659Notes

Reaction equation

HRID 1425659 reaction equation
[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23]([O:25]N2C(=O)CCC2=O)=O)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39]>CN(C=O)C>[C:1]([O:5][C:6](=[O:33])[C:7]1[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][C:23](=[O:25])[NH:34][CH2:35][CH2:36][CH2:37][C:38]([OH:40])=[O:39])=[CH:11][CH:12]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 86629716HCID 86629716, compound

Product 1

HCID 67145507HCID 67145507, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-[10-(2,5-Dioxopyrrolidin-1-yloxycarbonyl)decyl]benzoic acid tert-butyl ester (300 mg, 0.65 mmol) was dissolved in DMF (3 ml) and 4-amino butyric acid (67 mg, 0.65 mmol). The mixture was stirred for 16 h under nitrogen. The solvent was removed under vacuum and AcOEt (35 ml) was added. The solution was washed with 0.2 N HCl and water (15 ml each). Sat. NaHCO3 was added (not intended) to the organic phase. DCM (50 ml) was added. Some of the organic phase was removed and DCM (100 ml) was added to the aqueous phase and allowed to stand overnight. The mixture was cooled on ice and the pH was adjusted to 1.9 with 4N HCl. The organic phase was isolated, dried over MgSO4 and concentrated under vacuum to yield on oil (220 mg, 76% yield).

Workup

  1. customThe solvent was removed under vacuum and AcOEt (35 ml)
  2. additionwas added
  3. washThe solution was washed with 0.2 N HCl and water (15 ml each)
  4. additionSat. NaHCO3 was added (not
  5. additionDCM (50 ml) was added
  6. customSome of the organic phase was removed
  7. additionDCM (100 ml) was added to the aqueous phase
  8. waitto stand overnight
  9. temperatureThe mixture was cooled on ice
  10. customThe organic phase was isolated
  11. dry with materialdried over MgSO4
  12. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-a12d7ebe6bce4ceaaf4aba91fe04b3a5
Source dataset
uspto-grants-2015_01
Patent number
US08933021B2

Reaction notes

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