(1S,2S,4R,8S,9S,11S,12R,13S,19S)-12,19-difluoro-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-[(3-methylphenyl)methyl]-6-azapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-dien-16-one → 4b,12-Difluoro-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-8-quinolin-2-ylmethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one
Reaction equation
[F:1][C@@:2]12[C@:15]3([CH3:16])[C:10](=[CH:11][C:12](=[O:17])[CH:13]=[CH:14]3)[C@@H:9]([F:18])[CH2:8][C@H:7]1[C@@H:6]1[CH2:19][C@@H:20]3[C@:24]([C:25](=[O:31])[CH2:26][O:27]C(=O)C)([C@@:5]1([CH3:43])[CH2:4][C@@H:3]2[OH:44])[CH2:23][N:22]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1)[CH2:21]3.F[C@@]12[C@]3(C)C(=CC(=O)C=C3)[C@@H](F)C[C@H]1[C@@H]1C[C@@H]3[C@](C(=O)CO)([C@@]1(C)C[C@@H]2O)CN(CC1C=CC=C(C)C=1)C3>>[F:1][C:2]12[C:15]3([CH3:16])[C:10](=[CH:11][C:12](=[O:17])[CH:13]=[CH:14]3)[CH:9]([F:18])[CH2:8][CH:7]1[CH:6]1[CH2:19][CH:20]3[C:24]([C:25](=[O:31])[CH2:26][OH:27])([C:5]1([CH3:43])[CH2:4][CH:3]2[OH:44])[CH2:23][N:22]([CH2:32][C:33]1[CH:42]=[CH:41][C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[N:34]=1)[CH2:21]3Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared from compound 11 (130 mg, 0.215 mmol) following the procedure described in Example 5 for the synthesis of compound 9. Compound 12 (68 mg, 56% yield) was obtained.
Sources & evidence
- ORD record
- ord-7b81a0f1b56c4e07842d6c281772dfcf
- Source dataset
- uspto-grants-2014_04
- Patent number
- US08710037B2
Reaction notes
Loading…