Acetic Acid → HCID 70194849, compound

HRID 1034473Notes

Reaction equation

HRID 1034473 reaction equation
[CH3:1][O:2][C:3]1[CH:41]=[CH:40][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:16][C:17]([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][C@H:12]2[CH2:36][N:37]=[N+]=[N-])=[O:10])=[CH:5][CH:4]=1.CO.[C:44]([OH:47])(=[O:46])[CH3:45]>C(OCC)(=O)C.[Pd]>[C:44]([OH:47])(=[O:46])[CH3:45].[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][O:8][C:9]([N:11]2[CH2:15][C@@H:14]([S:16][C:17]([C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH2:13][C@H:12]2[CH2:36][NH2:37])=[O:10])=[CH:40][CH:41]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 887MethanolHCID 57241986HCID 57241986, compound

Product 1

HCID 70194849HCID 70194849, compoundYield 94.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-azidomethyl-4-tritylthiopyrrolidine (17.27 g: 30.64 mmole) in a mixture of ethyl acetate (150 ml), methanol (200 ml), and acetic acid (2.63 ml: 46 mmole) is subjected to conventional hydrogenation over 5% palladium on carbon (5 g). After the reaction, the catalyst is filtered off and the filtrate is concentrated in vacuo to give (2S,4S)-1-p-methoxybenzyloxycarbonyl-2-aminomethyl-4-tritylthiopyrrolidine acetate (17.33 g) as a residue. The residue is dissolved in dichloromethane, washed with aqueous sodium hydrogen carbonate, and concentrated to give (2S,4S)-2-aminomethyl-1-p-methoxybenzyloxycarbonyl-4-tritylthiopyrrolidine (16.82 g).

Workup

  1. customAfter the reaction
  2. filtrationthe catalyst is filtered off
  3. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f0763ea95c5e435c87625d2c210a3174
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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