Ammonia → HCID 131716381, compound

HRID 1650827Notes

Reaction equation

HRID 1650827 reaction equation
[N:1]([N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C@@H: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][N:12]2[C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])[CH2:6][CH2:5]1)=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>N1C=CC=CC=1>[NH2:1][N:4]1[CH2:9][CH2:8][N:7]([CH2:10][C@@H:11]2[CH2:15][C@H:14]([S:16][C:17]([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH2:13][N:12]2[C:36]([O:38][CH2:39][C:40]2[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=2)=[O:37])[CH2:6][CH2:5]1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 131716380HCID 131716380, compound

Product 1

HCID 131716381HCID 131716381, compoundYield 73.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (2S,4S) 2-[(4-azidopiperizin-1-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (3.76 g) in pyridine (12 ml) was added triphenylphosphine (2.38 g) and the mixture was stirred at ambient temperature for 1 hour. To the reaction mixture was added concentrated ammonia (0.76 ml) and the mixture was allowed to stand overnight at ambient temperature. The reaction mixture was concentrated under reduced pressure and the residue was dissolved in ethyl acetate (100 ml). The solution was washed with saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo to give a residue. The residue was chromatographed on silica gel (100 g) eluting with a mixture of chloroform and methanol (10:1 V/V). The fractions containing the desired compound were collected and evaporated in vacuo to give (2S,4S)-2-[(4-aminopiperizin-1-yl)methyl]-1-(4-nitrobenzyloxycarbonyl)-4-(triphenylmethylthio)pyrrolidine (2.66 g).

Workup

  1. waitto stand overnight at ambient temperature
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  4. washThe solution was washed with saturated aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customto give a residue
  8. customThe residue was chromatographed on silica gel (100 g)
  9. washeluting with a mixture of chloroform and methanol (10:1 V/V)
  10. additionThe fractions containing the desired compound
  11. customwere collected
  12. customevaporated in vacuo

Sources & evidence

ORD record
ord-82d4f3e2d17d4d1993d74c91f6662259
Source dataset
uspto-grants-1990_05
Patent number
US04925838

Reaction notes

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