Sulfuric Acid → HCID 15567308, compound

HRID 1075356Notes

Reaction equation

HRID 1075356 reaction equation
[CH3:1][C:2](=[CH2:4])[CH3:3].[NH:5]([C:23]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:24])[C@@H:6]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11].S(=O)(=O)(O)O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[NH:5]([C:23]([O:25][CH2:26][C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)=[O:24])[C@@H:6]([C:13]([O:15][CH2:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)=[O:14])[CH2:7][CH2:8][CH2:9][C:10]([O:12][C:2]([CH3:3])([CH3:1])[CH3:4])=[O:11]

Participants

6

Reactant 4

HCID 1118Sulfuric Acid2×HCID 8255IsobutyleneHCID 516892Sodium BicarbonateHCID 15567305HCID 15567305, compound

Product 1

HCID 15567308HCID 15567308, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

400 ml of isobutylene are added to a solution of 40 g (approx. 104 mmoles) of Z-D-Aad-OBzl in 400 ml of methylene chloride, followed, at -20°, by 4 ml of concentrated sulfuric acid. The mixture is allowed to stand in an autoclave for 3 days at room temperature. The batch is stirred with NaHCO3 solution in order to neutralize the sulfuric acid and the excess isobutylene is removed by means of a stream of nitrogen. The methylene chloride phase is extracted by shaking with water and is dried over Na2SO4 and concentrated. This leaves 46.3 g of an oil, which is chromatographed on 500 g of silica gel using a 9:1 mixture of methylene chloride and acetone. The eluate, which contains Z-Aad-(OBut)-OBzl, is concentrated. Yield: 42.35 g of a pale oil (92%).

Workup

  1. customthe excess isobutylene is removed by means of a stream of nitrogen
  2. extractionThe methylene chloride phase is extracted
  3. dry with materialis dried over Na2SO4
  4. concentrationconcentrated
  5. customThis leaves 46.3 g of an oil, which is chromatographed on 500 g of silica gel using
  6. additiona 9:1 mixture of methylene chloride and acetone
  7. concentrationis concentrated

Sources & evidence

ORD record
ord-f11aaf851a11493a9eec3e1e66558281
Source dataset
uspto-grants-1983_07
Patent number
US04395400

Reaction notes

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