Gamma-Aminobutyric Acid → 5-[9-(3-Carboxy-propylcarbamoyl)-nonyloxy]-isophthalic Acid Di-tert-butyl Ester

HRID 1022421Notes

Reaction equation

HRID 1022421 reaction equation
[C:1]([O:5][C:6](=[O:40])[C:7]1[CH:19]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](ON2C(=O)CCC2=O)=[O:31])[CH:17]=[C:9]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:8]=1)([CH3:4])([CH3:3])[CH3:2].[NH2:41][CH2:42][CH2:43][CH2:44][C:45]([OH:47])=[O:46].CCN(C(C)C)C(C)C>CN(C=O)C>[C:13]([O:12][C:10](=[O:11])[C:9]1[CH:17]=[C:18]([O:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][C:30](=[O:31])[NH:41][CH2:42][CH2:43][CH2:44][C:45]([OH:47])=[O:46])[CH:19]=[C:7]([C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:40])[CH:8]=1)([CH3:14])([CH3:15])[CH3:16]

Participants

5

Reactant 3

HCID 119Gamma-Aminobutyric AcidHCID 81531DiisopropylethylamineHCID 86630519HCID 86630519, compound

Product 1

HCID 684424855-[9-(3-Carboxy-propylcarbamoyl)-nonyloxy]-isophthalic Acid Di-tert-butyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-[9-(2,5-Dioxo-pyrrolidin-1-yloxycarbonyl)-nonyloxy]-isophthalic acid di-tert-butyl ester (100 mg, 0.18 mmol) was dissolved in dry DMF (2 ml). 4-Aminobutyric acid (GABA, 23 mg, 0.2 mmol) and DIPEA (0.05 ml) was added. The mixture was stirred under nitrogen for 2 days. The mixture was concentrated. The residue was dissolved in EtOAc and washed with 0.1 N HCl (2×) and brine (1×), dried (Na2SO4) and concentrated to give a clear syrup.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionThe residue was dissolved in EtOAc
  3. washwashed with 0.1 N HCl (2×) and brine (1×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. customto give a clear syrup

Sources & evidence

ORD record
ord-c0904acc259540038d71cf6ca2739eb3
Source dataset
uspto-grants-2014_05
Patent number
US08722620B2

Reaction notes

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