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4,6-Dimethyl-2-(4-nitrobenzyloxycarbonylthio)pyrimidine → (2R,4R)-1-p-nitrobenzyloxycarbonyl-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine

HRID 1088282
Notes
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Reaction equation

HRID 1088282 reaction equation
[N+:1]([C:4]1[CH:22]=[CH:21][C:7]([CH2:8][O:9][C:10](SC2N=C(C)C=C(C)N=2)=[O:11])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:23]([O:27][C:28]([CH2:30][CH2:31][CH2:32][CH2:33][C@@H:34]1[CH2:38][C@@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:36][NH:35]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>O1CCCC1.C(OCC)(=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][O:9][C:10]([N:35]2[CH2:36][C@H:37]([O:39][Si:40]([C:43]([CH3:46])([CH3:45])[CH3:44])([CH3:42])[CH3:41])[CH2:38][C@H:34]2[CH2:33][CH2:32][CH2:31][CH2:30][C:28]([O:27][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:29])=[O:11])=[CH:21][CH:22]=1)([O-:3])=[O:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 135043164,6-Dimethyl-2-(4-nitrobenzyloxycarbonylthio)pyrimidineHCID 15671521(2R,4R)-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine

Product 1

HCID 15671522(2R,4R)-1-p-nitrobenzyloxycarbonyl-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent
HCID 8857
Ethyl Acetate
Solvent

Procedure

S-p-Nitrobenzyloxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (719 mg) was added to 770 mg of (2R,4R)-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine in 7 ml of tetrahydrofuran and stirred at room temperature for 2 hours. The reaction mixture was diluted with ethyl acetate, washed successively with brine, dilute hydrochloric acid and brine, dried over anhydrous sodium sulfate and distilled to remove the solvent. The residue was purified by silica gel chromatography to obtain (2R,4R)-1-p-nitrobenzyloxycarbonyl-2-(4-t-butoxycarbonylbutyl)-4-t-butyldimethylsilyloxypyrrolidine.

Workup

  1. washwashed successively with brine, dilute hydrochloric acid and brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationdistilled
  4. customto remove the solvent
  5. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-7dde82a565624ae0977c5122641c87fc
Source dataset
uspto-grants-1990_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04962103

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes