Methyl-(2S,3S)-1-{[(3-chloro-4-cyano-2-methylphenyl)amino]-carbonyl}-3-(tert-butyl-dimethylsilanyloxy)-pyrrolidine-2-carboxylate → Methyl (2S,4R)-1-{[(3-chloro-4-cyano-2-methylphenyl)amino]-carbonyl}-4-(tert-butyldimethylsilanyloxy)pyrrolidine-2-carboxylate
Reaction equation
[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([NH:10][C:11]([N:13]2[CH2:17][C@H:16]([OH:18])[CH2:15][C@H:14]2[C:19]([O:21][CH3:22])=[O:20])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9].COC([C@@H]1[C@@H](O[Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])CCN1C(NC1C=CC(C#N)=C(Cl)C=1C)=O)=O>>[Cl:1][C:2]1[C:3]([CH3:23])=[C:4]([NH:10][C:11]([N:13]2[CH2:17][C@H:16]([O:18][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35])[CH2:15][C@H:14]2[C:19]([O:21][CH3:22])=[O:20])=[O:12])[CH:5]=[CH:6][C:7]=1[C:8]#[N:9]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from compound 56B (150 mg, 0.44 mmol) in a manner analogous to that described for compound 55B to afford a white solid (156.3 mg, 79%), mp 129-131° C. HPLC: 3.38 min (retention time) (Conditions: YMC S-5 C-18 (4.6×250 mm), eluting with 0-100% B, 4 min gradient. (A=90% H2O-10% CH3CN-0.1% TFA and B=10% H2O-90% CH3CN-0.1% TFA); Flow rate at 4 mL/min. UV detection at 220 nm. Chiral HPLC: retention time=9.80 min (99.9%); Conditions: AD (4.6×250 mm); Eluted with 20% isopropanol in heptane for 30 min at 1 mL/min. MS (ES) m/z 452 [M+H]+.
Sources & evidence
- ORD record
- ord-afbce9f5e7d24d0387397cf31cbb3d9b
- Source dataset
- uspto-grants-2010_08
- Patent number
- US07772267B2
Reaction notes
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