Sodium Hydroxide → HCID 56996121, compound

HRID 1590499Notes

Reaction equation

HRID 1590499 reaction equation
[NH2:1][CH2:2][C@@H:3]1[CH2:7][C@@H:6]([O:8][Si:9]([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10])[CH2:5][N:4]1[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=1)=[O:17].[Cl:29][CH:30]([CH3:34])[C:31](Cl)=[O:32].[OH-].[Na+]>O1CCCC1.O>[Si:9]([O:8][C@H:6]1[CH2:5][N:4]([C:16]([O:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([N+:26]([O-:28])=[O:27])=[CH:22][CH:21]=2)=[O:17])[C@H:3]([CH2:2][NH:1][C:31](=[O:32])[CH:30]([Cl:29])[CH3:34])[CH2:7]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 1110192-Chloropropionyl chlorideHCID 57114383HCID 57114383, compound

Product 1

HCID 56996121HCID 56996121, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-2-aminomethyl-4-(t-butyldimethylsilyloxy)-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine (15 g) in a mixture of tetrahydrofuran (100 ml) and water (50 ml) was added dropwise 2-chloropropionylchloride (4.27 ml) with stirring under ice-cooling, keeping the pH 9-10 with 4N sodium hydroxide. The mixture was stirred at the same temperature for 1 hour. The reaction mixture was evaporated in vacuo to remove the organic layer. The resulting residue was extracted twice with ethyl acetate (100 ml). The extract was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give (2S,4R)-4-(t-butyldimethylsilyloxy)-2-(2-chloropropionyl)aminomethyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine (18.36 g).

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at the same temperature for 1 hour
  3. customThe reaction mixture was evaporated in vacuo
  4. customto remove the organic layer
  5. extractionThe resulting residue was extracted twice with ethyl acetate (100 ml)
  6. washThe extract was washed with saturated aqueous sodium chloride
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-995246fd308d4bf1b032f0acd1f44320
Source dataset
uspto-grants-1993_04
Patent number
US05202437

Reaction notes

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