Sodium Chloride → HCID 57024843, compound

HRID 1613989Notes

Reaction equation

HRID 1613989 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][CH2:30][C:31](Cl)=[O:32].[OH-].[Na+].[Cl-].[Na+]>O.O1CCCC1>[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])[CH2:30][Cl:29])[CH2:7]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 6577Chloroacetyl chlorideHCID 14798Sodium HydroxideHCID 57114383HCID 57114383, compound

Product 1

HCID 57024843HCID 57024843, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,4R)-2-aminomethyl-4-t-butyldimethylsilyloxy-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (30.0 g) in water (150 ml) and tetrahydrofuran (450 ml) was added chloroacetyl chloride (6.4 ml) below 10° C., keeping the pH between 8-9 with 4N aqueous sodium hydroxide. The reaction mixture was poured into saturated aqueous sodium chloride (150 ml), the organic layer was separated, and the aqueous solution was extracted twice with ethyl acetate (100 ml). The organic layer was combined and washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo to give crude (2S,4R)-4-t-butyldimethylsilyloxy-2-(chloroacetamido)methyl-1-(4-nitrobenzyloxycarbonyl)-pyrrolidine.

Workup

  1. customthe organic layer was separated
  2. extractionthe aqueous solution was extracted twice with ethyl acetate (100 ml)
  3. washwashed with saturated aqueous sodium chloride
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-335d0285623c4c258c6a85419a52cdc8
Source dataset
uspto-grants-1993_03
Patent number
US05194624

Reaction notes

Loading…