Sulfuric Acid → Acetic acid, [(1-methylethyl)thio][[(phenylmethoxy)carbonyl]amino]-

HRID 1080376Notes

Reaction equation

HRID 1080376 reaction equation
O[CH:2]([C:14]([OH:16])=[O:15])[NH:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[CH:17]([SH:20])([CH3:19])[CH3:18].OS(O)(=O)=O>C(O)(=O)C>[CH:17]([S:20][CH:2]([C:14]([OH:16])=[O:15])[NH:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5])([CH3:19])[CH3:18]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 63642-PropanethiolHCID 35095062-(((Benzyloxy)carbonyl)amino)-2-hydroxyacetic acid

Product 1

HCID 11346620Acetic acid, [(1-methylethyl)thio][[(phenylmethoxy)carbonyl]amino]-Yield 94%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

α-hydroxy-N-benzyloxycarbonylglycine 22A (5.57 g, 0.027 mol) of Example 1 was stirred with isopropylmercaptan (8.29 g, 0.11 mol) in glacial acetic acid (26.5 mL) at 0° C. Conc H2SO4 (0.27 mL) was added and the mixture stirred for 2 days at room temperature. The mixture was then poured into ice and the organic layer extracted with ethyl acetate. The ethyl acetate solution was washed with water, 5% NaHCO3, dried over MgSO4, solvent removed to give 22B in 94% yield. This was used without further purification.

Workup

  1. additionThe mixture was then poured into ice
  2. extractionthe organic layer extracted with ethyl acetate
  3. washThe ethyl acetate solution was washed with water, 5% NaHCO3
  4. dry with materialdried over MgSO4, solvent
  5. customremoved

Sources & evidence

ORD record
ord-b3b359cee4614acc9ed20aa7c9d88e9e
Source dataset
uspto-grants-1996_12
Patent number
US05580979

Reaction notes

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