L-Prolinamide → (2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine

HRID 1650822Notes

Reaction equation

HRID 1650822 reaction equation
CS(O[CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9][N:8]1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])(=O)=O.[C:45]([C@@H:48]1[CH2:52][CH2:51][CH2:50][NH:49]1)(=[O:47])[NH2:46]>CN(C)C=O>[C:45]([C@@H:48]1[CH2:52][CH2:51][CH2:50][N:49]1[CH2:6][C@@H:7]1[CH2:11][C@H:10]([S:12][C:13]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:9][N:8]1[C:32]([O:34][CH2:35][C:36]1[CH:41]=[CH:40][C:39]([N+:42]([O-:44])=[O:43])=[CH:38][CH:37]=1)=[O:33])(=[O:47])[NH2:46]

Participants

4

Reactant 2

HCID 111306L-ProlinamideHCID 15056119(2S,4S)-2-mesyloxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Product 1

HCID 15056121(2S,4S)-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidineYield 25.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (2S,4S)-2-(methanesulfonyloxy)methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (3.0 g) in dimethylformamide (30 ml) was added (2S)-2-carbamoylpyrrolidine (10.76 g) and the mixture was stirred at 100°-110° C. for 5 hours. The reaction mixture was poured into ice-water (100 ml). The resulting precipitates were collected by filtration and washed with water (100 ml). The precipitates were dissolved in ethyl acetate (80 ml) and the solution was washed with aqueous sodium chloride, dried over anhydrous magnesium sulfate and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (100 g) eluting with a mixture of dichloromethane and acetone (9:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S ,4S )-2-[(2S)-2-carbamoylpyrrolidin-1-yl]methyl-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (0.78 g).

Workup

  1. customThe resulting precipitates
  2. filtrationwere collected by filtration
  3. washwashed with water (100 ml)
  4. dissolutionThe precipitates were dissolved in ethyl acetate (80 ml)
  5. washthe solution was washed with aqueous sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customevaporated in vacuo
  8. customto give a residue
  9. customThe residue was chromatographed on silica gel (100 g)
  10. washeluting with a mixture of dichloromethane and acetone (9:1 V/V)
  11. additionThe fractions containing the desired compound
  12. customwere collected
  13. customevaporated in vacuo

Sources & evidence

ORD record
ord-1691b830f47e4f9fa24ede5d76de5e78
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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