Triethylamine → HCID 56629981, compound

HRID 2371407Notes

Reaction equation

HRID 2371407 reaction equation
[C:1]([O:4][CH2:5][C@@H:6]1[CH2:10][C@@H:9]([OH:11])[CH2:8][NH:7]1)(=[O:3])[CH3:2].[N+:12]([C:15]1[CH:33]=[CH:32][C:18]([CH2:19][O:20][C:21](SC2N=C(C)C=C(C)N=2)=[O:22])=[CH:17][CH:16]=1)([O-:14])=[O:13].C(N(CC)CC)C>O.O1CCCC1.C(OCC)(=O)C>[N+:12]([C:15]1[CH:16]=[CH:17][C:18]([CH2:19][O:20][C:21]([N:7]2[CH2:8][C@H:9]([OH:11])[CH2:10][C@H:6]2[CH2:5][O:4][C:1](=[O:3])[CH3:2])=[O:22])=[CH:32][CH:33]=1)([O-:14])=[O:13]

Participants

7

Reactant 3

HCID 8471TriethylamineHCID 135043164,6-Dimethyl-2-(4-nitrobenzyloxycarbonylthio)pyrimidineHCID 56633484HCID 56633484, compound

Product 1

HCID 56629981HCID 56629981, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,4R)-2-acetoxymethyl-4-hydroxypyrrolidine (22.66 g) in water (100 ml), a solution of S-p-nitrobenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (34.45 g) in tetrahydrofuran (453 ml) was added at room temperature, followed by addition of triethylamine (22.54 ml). The resulting mixture was stirred at the same temperature for 30 minutes and diluted with ethyl acetate. The reaction mixture was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution and dried over magnesium sulfate, followed by removal of the solvent. The residue was purified by silica gel column chromatography to give (2S,4R)-1-p-nitrobenzyloxycarbonyl-2-acetoxymethyl4-hydroxypyrrolidine.

Workup

  1. washThe reaction mixture was washed successively with dilute hydrochloric acid and aqueous sodium chloride solution
  2. dry with materialdried over magnesium sulfate
  3. customfollowed by removal of the solvent
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-d07369521ec9443aa5407e0e6718f301
Source dataset
uspto-grants-1992_03
Patent number
US05093328

Reaction notes

Loading…