Dimethylformamide → HCID 57190520, compound

HRID 1737072Notes

Reaction equation

HRID 1737072 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([O:15][CH2:16][C@H:17]3[N:21]([CH2:22][CH2:23][CH2:24][C:25]4[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=4)[C:20](=[O:31])[C@H:19]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:18]3)=[C:11]([N+:37]([O-])=O)[CH:10]=2)=[CH:5][CH:4]=1)#[N:2].CN(C)C=O>C(O)C.[Pd]>[NH2:37][C:11]1[CH:10]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[CH:14]=[CH:13][C:12]=1[O:15][CH2:16][C@H:17]1[N:21]([CH2:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:20](=[O:31])[C@H:19]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:18]1

Participants

5

Reactant 2

HCID 6228DimethylformamideHCID 22863912HCID 22863912, compound

Product 1

HCID 57190520HCID 57190520, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4 g of (3S,5S)-5-[(4'-cyano-3-nitro-4-biphenylyl)oxymethyl]-3-[(methoxycarbonyl)methyl]-1-(3-phenylpropyl)-2-pyrrolidinone are hydrogenated in 40 ml of ethanol and 10 ml of dimethylformamide with 1.5 g of palladium (10% on activated charcoal) under a hydrogen pressure of 3 bar at ambient temperature. After 40 minutes the catalyst is removed by suction filtering and the filtrate is evaporated down. The residue is divided between water and methylene chloride, the organic phase is separated off, dried with magnesium sulphate and evaporated down. Column chromatography on silica gel with methylene chloride/ethyl acetate (4:1) yields 2.9 g (77% of theory) of the desired compound. Melting point: 111°-112° C. Rf value: 0.37 (silica gel; 1,2-dichloroethane/ethyl acetate=3:1) Calculated: C 72.41 H 6.28 N 8.45 Found: 72.31 6.54 8.27

Workup

  1. customat ambient temperature
  2. customAfter 40 minutes the catalyst is removed by suction
  3. filtrationfiltering
  4. customthe filtrate is evaporated down
  5. customthe organic phase is separated off
  6. dry with materialdried with magnesium sulphate
  7. customevaporated down

Sources & evidence

ORD record
ord-3ce3f9a355df4e7a929e0c8c2f3dc93b
Source dataset
uspto-grants-1996_07
Patent number
US05541343

Reaction notes

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