Gamma-Aminobutyric Acid → HCID 178454267, compound

HRID 1373671Notes

Reaction equation

HRID 1373671 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:8]([O:12][C:13]([NH:15][C:16](=[N:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])SC)=[O:14])([CH3:11])([CH3:10])[CH3:9]>O1CCCC1.O>[C:23]([O:22][C:20]([N:19]=[C:16]([NH:15][C:13]([O:12][C:8]([CH3:11])([CH3:10])[CH3:9])=[O:14])[NH:1][CH2:2][CH2:3][CH2:4][C:5]([OH:7])=[O:6])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

5

Reactant 2

HCID 119Gamma-Aminobutyric AcidHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 178454267HCID 178454267, compoundYield 54%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

4-Aminobutyric acid (100 mg, 0.97 mmol) was dissolved in tetrahydrofuran (0.3 mL) and water (0.03 mL), combined with 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (340 mg, 1.2 mmol) and stirred at 60° C. overnight. The reaction solution was concentrated under reduced pressure, and the residue was subjected to a column chromatography to obtain 4-(2,3-di-tert-butoxycarbonylguanidino)butyric acid (compound 8; yield: 181 mg).

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ed5dc344f74740bc8d0b3042770309dc
Source dataset
uspto-grants-2007_01
Patent number
US07163921B1

Reaction notes

Loading…