Triethylamine → HCID 131730166, compound
Reaction equation
[C:1]([O:5][C:6](=[O:26])[CH2:7]/[N:8]=[CH:9]/[CH2:10][C:11]1([C:17]([CH3:25])([CH3:24])[O:18][SiH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[Cl:27][C:28]1[C:29]([F:46])=[C:30](/[CH:34]=[C:35](/[C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][C:39]=2[F:45])\[C:36]#[N:37])[CH:31]=[CH:32][CH:33]=1.C(N(CC)CC)C.C1CCN2C(=NCCC2)CC1>ClCCl.C(O)(C)(C)C>[C:1]([O:5][C:6]([CH:7]1[CH:34]([C:30]2[CH:31]=[CH:32][CH:33]=[C:28]([Cl:27])[C:29]=2[F:46])[C:35]([C:38]2[CH:43]=[CH:42][C:41]([Cl:44])=[CH:40][C:39]=2[F:45])([C:36]#[N:37])[CH:9]([CH2:10][C:11]2([C:17]([CH3:25])([CH3:24])[O:18][SiH2:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:16][CH2:15][CH:14]=[CH:13][CH2:12]2)[NH:8]1)=[O:26])([CH3:3])([CH3:4])[CH3:2]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
In a manner similar to the method described in Example 100b, [2-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enyl]-eth-(E)-ylideneamino]-acetic acid tert-butyl ester prepared in Example 117a (3.5 g, 9 mmol) was reacted with (Z)-3-(3-chloro-2-fluoro-phenyl)-2-(4-chloro-2-fluoro-phenyl)-acrylonitrile (2.3 g, 7 mmol) prepared in Example 52a, AgF (1.4 g, 11 mmol), and triethylamine (2.6 mL, 19 mmol) in dichloromethane (100 mL) at room temperature for 18 h, followed by the reaction with DBU (9 ml) in tert-butanol (10 mL) at 100° C. for 2 h to give rac-(2R,3S,4R,5S)-5-[1-(tert-butyl-dimethyl-silanyloxymethyl)-cyclohex-3-enylmethyl]-3-(3-chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-pyrrolidine-2-carboxylic acid tert-butyl ester as a white solid (2.6 g, 51%).
Sources & evidence
- ORD record
- ord-f12fdbee85f2419bb24ce986a9f14676
- Source dataset
- uspto-grants-2013_01
- Patent number
- US08354444B2
Reaction notes
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