Water → alpha-Benzyl-alpha-benzyloxycarbonylamino-gamma-butyrolactone

HRID 247178Notes

Reaction equation

HRID 247178 reaction equation
[CH2:1]([C:8]1([NH2:14])[CH2:13][CH2:12][O:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH2:21]([O:28][C:29](Cl)=[O:30])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.O>O1CCCC1.C(OCC)(=O)C>[CH2:1]([C:8]1([NH:14][C:29]([O:28][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:30])[CH2:13][CH2:12][O:11][C:9]1=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 10387Benzyl chloroformateHCID 140831243-amino-3-benzyldihydrofuran-2(3H)-one

Product 1

HCID 14083125alpha-Benzyl-alpha-benzyloxycarbonylamino-gamma-butyrolactone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 1.55 g of α-benzyl-α-amino-γ-butyrolactone in 16 ml of tetrahydrofuran is added 2.0 g of powdered sodium carbonate, followed by 1.27 ml of benzylchloroformate. After stirring at room temperature for 18 hours, water is added to dissolve the salt and the resulting mixture is diluted with 100 ml of ethyl acetate. It is washed with 50 ml of saturated aqueous sodium chloride. The aqueous phase is extracted with two 50 ml portions of ethyl acetate. The combined organic phase is dried (magnesium sulfate), filtered, and then concentrated. The residue is passed through 20 g of silica gel with ethyl acetate, and the filtrate concentrated to the title product as a white solid, 2.6 g.

Workup

  1. dissolutionto dissolve the salt
  2. washIt is washed with 50 ml of saturated aqueous sodium chloride
  3. extractionThe aqueous phase is extracted with two 50 ml portions of ethyl acetate
  4. dry with materialThe combined organic phase is dried (magnesium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. concentrationthe filtrate concentrated to the title product as a white solid, 2.6 g

Sources & evidence

ORD record
ord-1846ea14457446a2a4b5061bf02872e5
Source dataset
uspto-grants-1987_11
Patent number
US04705846

Reaction notes

Loading…