(2S,4S)-2-mesyloxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine → (2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine

HRID 1034480Notes

Reaction equation

HRID 1034480 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]1(=[O:55])[NH:49][C:48](=[O:50])[C:47]2=[CH:51][CH:52]=[CH:53][CH:54]=[C:46]12.[K]>CN(C)C=O>[N+:42]([C:39]1[CH:38]=[CH:37][C:36]([CH2:35][O:34][C:32]([N:8]2[CH2:9][C@@H:10]([S:12][C:13]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH2:11][C@H:7]2[CH2:6][N:49]2[C:45](=[O:55])[C:46]3=[CH:54][CH:53]=[CH:52][CH:51]=[C:47]3[C:48]2=[O:50])=[O:33])=[CH:41][CH:40]=1)([O-:44])=[O:43]

Participants

4

Reactant 2

HCID 15056119(2S,4S)-2-mesyloxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidineHCID 24194345Phthalimide potassium salt

Product 1

HCID 57302820(2s,4s)-1-p-Nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidineYield 65.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol methanesulfonate (4.39 g: 6.93 mmole) and potassium phthalimide (2.57 g: 2 eq.) in dimethylformamide (30 ml) is stirred at 70° C. for 6 hours. The reaction mixture is poured into ice water and the precipitate is filtered off. The precipitate is dissolved in ethyl acetate, washed with saturated brine, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene:ethyl acetate) to give (2S,4S)-1-p-nitrobenzyloxycarbonyl-2-phthalimidomethyl-4-tritylthiopyrrolidine (3.12 g). Yield: 64.3%. NMR δ(CDCl3) ppm: 1.40 to 2.30 (m, 2H), 2.60 to 3.08(m, 2H), 3.10 to 3.40(m, 1H), 3.55 to 4.23(m, 3H), 4.92, 5.06(ABq, J=12 Hz, 2H), 7.08 to 7.50 (m, 17H), 7.60 to 7.82(m, 4H), 8.10(d, J=9 Hz, 1H), 8.19(d, J=9 Hz, 1H). IR ν (CHCl3) cm-1 : 1720, 1701, 1607.

Workup

  1. filtrationthe precipitate is filtered off
  2. dissolutionThe precipitate is dissolved in ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue is purified by silica gel column chromatography (toluene:ethyl acetate)

Sources & evidence

ORD record
ord-74eb21011ccc4b4bae0beaf0144ca0ef
Source dataset
uspto-grants-1994_05
Patent number
US05317016

Reaction notes

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