Sulfuric Acid → HCID 18631486, compound

HRID 1194991Notes

Reaction equation

HRID 1194991 reaction equation
OS(O)(=O)=O.[CH3:6][C:7](=[CH2:9])[CH3:8].[CH2:10]([O:17][C:18]([NH:20][C:21](=[O:27])[C@@H:22]([C@H:24]([CH3:26])[OH:25])[NH2:23])=[O:19])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(=O)=O.CC(C)=O>C(Cl)Cl>[CH2:10]([O:17][C:18]([NH:20][C:21](=[O:27])[C@@H:22]([C@H:24]([CH3:26])[O:25][C:7]([CH3:9])([CH3:8])[CH3:6])[NH2:23])=[O:19])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 8255IsobutyleneHCID 18522661Acetone cardiceHCID 18631485HCID 18631485, compound

Product 1

HCID 18631486HCID 18631486, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Concentrated H2SO4 (0.1 ml) and isobutylene (35 ml, 390 mmol) are added to a suspension of N-benzyloxycarbonyl-D-threonineamide (4.2 g, 16.6 mmol) in methylene chloride (35 ml) kept in a pressure resistant vessel cooled with dry ice/acetone. The reaction vessel is sealed and the temperature is allowed to raise up to the room value. After 4 days, excess isobutylene is evaporated off and the organic solution is washed with aqueous 5% Na2CO3 (3×30 ml), 5% citric acid (20 ml) and then with water up to pH 6. The organic phase is dried over MgSO4 and concentrated to dryness yielding the compound of the title as a clear oil (4.62 g, 90%).

Workup

  1. customkept in a pressure resistant vessel
  2. customThe reaction vessel is sealed
  3. temperatureto raise up to the room value
  4. customexcess isobutylene is evaporated off
  5. washthe organic solution is washed with aqueous 5% Na2CO3 (3×30 ml), 5% citric acid (20 ml)
  6. dry with materialThe organic phase is dried over MgSO4
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9683ecd4bed64d5c989266f9b9cceee0
Source dataset
uspto-grants-1989_03
Patent number
US04816560

Reaction notes

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