Acetonitrile → HCID 178491727, compound

HRID 727646Notes

Reaction equation

HRID 727646 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:37]=[CH:36][C:7]([CH2:8][S:9][C@@H:10]2[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][CH:20]=3)=[O:16])[C@H:12]([C:28]([N:30]3[CH2:34][CH2:33][C@H:32]([NH2:35])[CH2:31]3)=[O:29])[CH2:11]2)=[CH:6][CH:5]=1.[N+:38]([C:41]1[CH:54]=[CH:53][C:44]([CH2:45][O:46][C:47](NC(=N)C)=[O:48])=[CH:43][CH:42]=1)([O-:40])=[O:39].[C:55](#[N:57])[CH3:56]>>[CH3:2][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH2:8][S:9][C@@H:10]2[CH2:14][N:13]([C:15]([O:17][CH2:18][C:19]3[CH:20]=[CH:21][C:22]([N+:25]([O-:27])=[O:26])=[CH:23][CH:24]=3)=[O:16])[C@H:12]([C:28]([N:30]3[CH2:34][CH2:33][C@H:32]([NH:35][C:55](=[NH:57])[CH2:56][C:47]([O:46][CH2:45][C:44]4[CH:43]=[CH:42][C:41]([N+:38]([O-:40])=[O:39])=[CH:54][CH:53]=4)=[O:48])[CH2:31]3)=[O:29])[CH2:11]2)=[CH:36][CH:37]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 67586147(2S,4S)-4-(4-Methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine HydrochlorideHCID 140352007HCID 140352007, compound

Product 1

HCID 178491727HCID 178491727, compound

Conditions

Temperature
53 °C

Procedure

A suspension of 1.00 g of (2S,4S)-4-(4-methoxybenzylthio)-2-[(3S)-3-aminopyrrolidin-1-ylcarbonyl]-1-(4-nitrobenzyloxycarbonyl)pyrrolidine hydrochloride [prepared as described in step (ii) above] and 0.47 g of N-(4-nitrobenzyloxycarbonyl)acetamidine in 20 ml of dry acetonitrile was stirred at 53° C. for 2 hours. The reaction mixture was then freed from impurities by filtration, and the filtrate was concentrated by evaporation under reduced pressure. The concentrate was purified by column chromatography through silica gel, using a 45:45:5 by volume mixture of methylene chloride, ethyl acetate and methanol as the eluent, to give 0.89 g of the title compound, as a powder.

Workup

  1. filtrationThe reaction mixture was then freed from impurities by filtration
  2. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  3. customThe concentrate was purified by column chromatography through silica gel
  4. additionby volume mixture of methylene chloride, ethyl acetate and methanol as the eluent

Sources & evidence

ORD record
ord-9b75c2f51f9a4add913451452883e51b
Source dataset
uspto-grants-1998_01
Patent number
US05712267

Reaction notes

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