Sodium Hydroxide → HCID 178427482, compound

HRID 1252529Notes

Reaction equation

HRID 1252529 reaction equation
[S:1]([N:11]1[CH2:13][C@H:12]1[C:14]([O:16]C)=[O:15])([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].[OH-].[Na+].[NH2:20][C@H:21]([C:28]([OH:30])=[O:29])[CH2:22][C:23]1[N:27]=[CH:26][NH:25][CH:24]=1>CO>[C:28]([C@@H:21]([NH:20][CH2:13][C@H:12]([NH:11][S:1]([C:4]1[CH:5]=[CH:6][C:7]([CH3:8])=[CH:9][CH:10]=1)(=[O:2])=[O:3])[C:14]([OH:16])=[O:15])[CH2:22][C:23]1[N:27]=[CH:26][NH:25][CH:24]=1)([OH:30])=[O:29]

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 10445076(S)-Methyl 1-tosylaziridine-2-carboxylateHCID 178419078HCID 178419078, compound

Product 1

HCID 178427482HCID 178427482, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of methyl (2S)-1-tosyl-2-aziridinecarboxylate (1.04 g) in methanol was added to 1N aqueous sodium hydroxide (4.1 ml) in an ice bath and the mixture was stirred for 50 minutes at the same temperature. To the resulting solution were added L-histidine (2.11 g) and sodium hydroxide (730 mg) and the mixture was refluxed for 1.5 hours. After removal of the solvent in vacuo, the residue was dissolved in water and adjusted to pH 4 with 2N sulfuric acid. The solution was subjected to a column of "Diaion HP-20" (150 ml) and the column was washed with water. The elution was carried out with a mixture of water and methanol (1:1 400 ml). The eluate was evaporated in vacuo and the residue was chromatographed on a silica gel (100 g) column with a mixutre of chloroform, methanol and 28% aqueous ammonia (5:3:1) as an eluent to give (2S)-3-[[(1S)-1-carboxy-2 -(4-imidazolyl)ethyl]amino]-2-tosylaminopropionic acid (485 mg).

Workup

  1. temperaturethe mixture was refluxed for 1.5 hours
  2. customAfter removal of the solvent in vacuo
  3. dissolutionthe residue was dissolved in water
  4. wash" (150 ml) and the column was washed with water
  5. washThe elution
  6. additionwas carried out with a mixture of water and methanol (1:1 400 ml)
  7. customThe eluate was evaporated in vacuo
  8. customthe residue was chromatographed on a silica gel (100 g) column with a mixutre of chloroform, methanol and 28% aqueous ammonia (5:3:1) as an eluent

Sources & evidence

ORD record
ord-6be144fc646d48ccb79eae7d9eb9a43c
Source dataset
uspto-grants-1988_05
Patent number
US04743614

Reaction notes

Loading…