Diisopropylethylamine → (R)-1-(3-Benzyloxyphenylsulfonyl)-3-(tert-butoxycarbonylamino) pyrrolidine
Reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.[C:28]([O:32][C:33]([NH:35][C@@H:36]1[CH2:40][CH2:39][NH:38][CH2:37]1)=[O:34])([CH3:31])([CH3:30])[CH3:29]>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([S:15]([N:38]2[CH2:39][CH2:40][C@@H:36]([NH:35][C:33]([O:32][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:34])[CH2:37]2)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a stirred solution of 3-benzyloxyphenylsulfonyl chloride, as described above in Step C, (1.8 g, 7.2 mmol) in CH2Cl2 (50 mL) was added N,N-diisopropylethylamine (1.8 mL, 10.3 mmol) followed by (R)-3-(tert-butoxycarbonylamino)pyrrolidine (1.77 g, 9.5 mmol) and the reaction mixture was stirred at ambient temperature for 4 hours. The mixture was washed with 10% aqueous citric acid (75 mL), then water (50 mL), then saturated aqueous NaHCO3 (50 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash column chromatography on silica, eluting with hexane—20% EtOAc to yield the desired product as a white solid.
Workup
- washThe mixture was washed with 10% aqueous citric acid (75 mL)
- dry with materialThe organic layer was dried over MgSO4
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe crude product was purified by flash column chromatography on silica
- washeluting with hexane—20% EtOAc
Sources & evidence
- ORD record
- ord-5c5175eff5a2435ea9b83f77fc12023c
- Source dataset
- uspto-grants-2002_08
- Patent number
- US06441017B1
Reaction notes
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