Water → HCID 20285448, compound

HRID 127623Notes

Reaction equation

HRID 127623 reaction equation
C([O:5][C:6](=[O:24])[CH2:7][N:8]([C:15](=[O:23])[CH:16]([CH3:22])[CH2:17][S:18][C:19](=[O:21])[CH3:20])[CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)(C)(C)C.C[Si](I)(C)C.O.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:19]([S:18][CH2:17][CH:16]([CH3:22])[C:15]([N:8]([CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1)[CH2:7][C:6]([OH:24])=[O:5])=[O:23])(=[O:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 85247Trimethylsilyl iodideHCID 516892Sodium BicarbonateHCID 20285466HCID 20285466, compound

Product 1

HCID 20285448HCID 20285448, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-(3-acetylthio-2-methylpropanoyl)-N-cyclohexylglycine t-butyl ester (36.4 g, 0.101 mol) in 300 ml of methylene chloride was added trimethylsilyl iodide (20.4 g, 0.102 mol). After stirring at room temperature for 1.75 hours 50 ml of water was added, followed in 10 min. by 500 ml of saturated sodium bicarbonate solution. An emulsion formed which was separated by centrifuging. The aqueous solution was separated, acidified with concentrated hydrochloric acid, and extracted with ethyl acetate. The extracts were dried, filtered, and concentrated to yield 25.6 g (83.4%) of N-(3-acetylthio-2-methylpropanoyl)-N-cyclohexylglycine as a pale yellow oil. The compound was characterized as its DCHA salt, prepared by dissolving the acid in ether and adding DCHA to pH 8-9. The salt was isolated as a white crystalline solid, m.p. 142°-144°.

Workup

  1. additionwas added
  2. customAn emulsion formed which
  3. customwas separated by centrifuging
  4. customThe aqueous solution was separated
  5. extractionextracted with ethyl acetate
  6. customThe extracts were dried
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-a24356fe42244f748e0083398e6672ff
Source dataset
uspto-grants-1981_03
Patent number
US04256761

Reaction notes

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