HCID 20285448, compound → HCID 20285455, compound

HRID 127624Notes

Reaction equation

HRID 127624 reaction equation
C([S:4][CH2:5][CH:6]([CH3:20])[C:7]([N:9]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:10][C:11]([OH:13])=[O:12])=[O:8])(=O)C>N>[SH:4][CH2:5][CH:6]([CH3:20])[C:7]([N:9]([CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1)[CH2:10][C:11]([OH:13])=[O:12])=[O:8]

Participants

3

Reactant 1

HCID 20285448HCID 20285448, compound

Product 1

HCID 20285455HCID 20285455, compoundYield 0%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To N-(3-Acetylthio-2-methylpropanoyl)-N-cyclohexylglycine (5.1 g, 16.9 mol) was added 100 ml of ammonia-saturated methanol, and the resulting solution stirred for 2.5 hours at room temperature under nitrogen. The solution was concentrated and the residue dissolved in methanol and passed through a column of AG-50W-X2 cation exchange resin. Those fractions showing a positive nitroprusside test were combined and concentrated. This material was then purified by medium pressure liquid chromatography eluting with ethyl acetate/hexane/acetic acid, 48:48:2 to give 0.7 g of N-(3-mercapto-2-methylpropanoyl)-N-cyclohexylglycine as an oil. The compound was characterized as its DCHA salt, prepared by dissolving the acid in ether and adding DCHA to pH 9. The salt was isolated as a white crystalline solid, m.p. 158°-160°.

Workup

  1. concentrationThe solution was concentrated
  2. dissolutionthe residue dissolved in methanol
  3. concentrationconcentrated
  4. customThis material was then purified by medium pressure liquid chromatography
  5. washeluting with ethyl acetate/hexane/acetic acid, 48:48:2

Sources & evidence

ORD record
ord-c73de5866cee4304853ab632c739788c
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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