Water → (2S,4S)-2-(4-azidomethyl-1,3-dioxolan-2-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

HRID 37270Notes

Reaction equation

HRID 37270 reaction equation
C([S:4][C@@H:5]1[CH2:9][N:8]([C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[C@H:7]([CH:23]2[O:27][CH:26]([CH2:28]Br)[CH2:25][O:24]2)[CH2:6]1)(=O)C.[N-:30]=[N+:31]=[N-:32].[Na+].O.C(OCC)(=O)C>CN(C)C=O>[N:30]([CH2:28][CH:26]1[CH2:25][O:24][CH:23]([C@@H:7]2[CH2:6][C@H:5]([SH:4])[CH2:9][N:8]2[C:10]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)=[O:11])[O:27]1)=[N+:31]=[N-:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 33557Sodium AzideHCID 57113127(2S,4S)-4-acetylthio-2-(4-bromomethyl-1,3-dioxolan-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidine

Product 1

HCID 18638804(2S,4S)-2-(4-azidomethyl-1,3-dioxolan-2-yl)-4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidineYield 70.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2S, 4S )-4-acetylthio-2-(4-bromomethyl1,3-dioxolan-2-yl)-1- (4-nitrobenzyloxycarbonyl)pyrrolidine (1.67 g) and sodium azide (0.24 g) in N,N-dimethylformamide (25 ml) was stirred at 60° C. for 1.5 hours, and the mixture was poured into a mixture of water (250 ml) and ethyl acetate (200 ml). The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated. The residue was dissolved in a mixture of methanol (8 ml) and tetrahydrofuran (8 ml), and then deacetylated by reacting the resultant product with 28% solution of sodium methoxide in methanol (0.7 ml) to give (2S,4S)-2-(4-azidomethyl-1,3-dioxolan-2-yl) -4-mercapto-1-(4-nitrobenzyloxycarbonyl)pyrrolidine (0.99 g) in substantially the same manner as that of Preparation 7-1).

Workup

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. dissolutionThe residue was dissolved in a mixture of methanol (8 ml) and tetrahydrofuran (8 ml)

Sources & evidence

ORD record
ord-e36801e97c5d4d509b948795280b52b0
Source dataset
uspto-grants-1995_05
Patent number
US05420122

Reaction notes

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