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Water → (2S,4S)-2-mesyloxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

HRID 1034479
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Reaction equation

HRID 1034479 reaction equation
[N+:1]([C:4]1[CH:40]=[CH:39][C:7]([CH2:8][O:9][C:10]([N:12]2[CH2:16][C@@H:15]([S:17][C:18]([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH2:14][C@H:13]2[CH2:37][OH:38])=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].C(N(CC)CC)C.[CH3:48][S:49](Cl)(=[O:51])=[O:50].O>ClCCl>[CH3:48][S:49]([O:38][CH2:37][C@@H:13]1[CH2:14][C@H:15]([S:17][C:18]([C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:16][N:12]1[C:10]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:40][CH:39]=1)=[O:11])(=[O:51])=[O:50]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 15056118(2S,4S)-2-hydroxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidine

Product 1

HCID 15056119(2S,4S)-2-mesyloxymethyl-N-(p-nitrobenzyloxycarbonyl)-4-tritylthiopyrrolidineYield 85.2%

Reagents, catalysts & solvents

1
HCID 6344DichloromethaneSolvent

Procedure

To a solution of (2S,4S)-1-p-nitrobenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol (5.0 g: 9.01 mmole) in dichloromethane (50 ml) stirring at -15° C., triethylamine (1.63 ml: 1.3 eq.) and methanesulfonyl chloride (0.85 ml: 1.1 eq.) are added. The mixture is stirred at -15° to -10° C. for 30 minutes. The reaction mixture is poured into water and extracted with dichloromethane. The extract is successively washed with dilute hydrochloric acid, aqueous sodium hydrogen carbonate, and water, dried over magnesium sulfate, and concentrated in vacuo. The residue is purified by silica gel column chromatography (toluene: ethyl acetate=9:1) to give (2S,4S)-1-p-nitrobenzyloxycarbonyl-4-tritylthiopyrrolidine-2-methanol methanesulfonate (4.86 g). Yield: 85.2%. NMR δ(CDCl3) ppm: 1.65 to 1.93(m, 1H), 2.00 to 2.26(m, 1H), 2.68 to 2.92(m, 3H), 2.96(s, 3H), 3.78 to 3.98(m, 1H), 4.16 to 4.30(m, 1H), 4.38 to 4.52(m, 1H), 5.11(br s, 2H), 7.08 to 7.52(m, 17H), 8.24(d, J=9 Hz, 2H). IR ν (CHCl3) cm-1 : 1699, 1606.

Workup

  1. extractionextracted with dichloromethane
  2. washThe extract is successively washed with dilute hydrochloric acid, aqueous sodium hydrogen carbonate, and water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by silica gel column chromatography (toluene: ethyl acetate=9:1)

Sources & evidence

ORD record
ord-94771a4468d641b28e1ce1a380baa10e
Source dataset
uspto-grants-1994_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05317016

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes