(1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid → (1aR,3aR,5S,7aR,15aS,Z)-5-(2-(4-ethynylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylic acid
Reaction equation
[C:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[C:16]([O:18][C@H:19]3[CH2:44][CH2:43][C@H:22]4[C:23](=[O:42])[N:24]([CH3:41])[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][C@@H:31]5[CH2:36][C@@:32]5([C:37]([O:39]C)=[O:38])[NH:33][C:34](=[O:35])[C@@H:21]4[CH2:20]3)[C:15]3[C:10](=[C:11]([CH3:47])[C:12]([O:45][CH3:46])=[CH:13][CH:14]=3)[N:9]=2)[S:6][CH:7]=1)#[CH:2].C(OC([C@@H]1C[C@H](O[Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)CC[C@H]1C(O)=O)=O)(C)(C)C>>[C:1]([C:3]1[N:4]=[C:5]([C:8]2[CH:17]=[C:16]([O:18][C@H:19]3[CH2:44][CH2:43][C@H:22]4[C:23](=[O:42])[N:24]([CH3:41])[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][C@@H:31]5[CH2:36][C@@:32]5([C:37]([OH:39])=[O:38])[NH:33][C:34](=[O:35])[C@@H:21]4[CH2:20]3)[C:15]3[C:10](=[C:11]([CH3:47])[C:12]([O:45][CH3:46])=[CH:13][CH:14]=3)[N:9]=2)[S:6][CH:7]=1)#[CH:2]Participants
3
Reactant 2
HCID 58282618(1R,2R,4R)-2-(tert-butoxycarbonyl)-4-(tert-butyldiphenylsilyloxy)cyclohexanecarboxylic acid
HCID 88050652(1aR,3aR,5S,7aR,15aS,Z)-methyl 5-(2-(4-ethynylthiazol-2-yl)-7-methoxy-8-methylquinolin-4-yloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylateProduct 1
Procedure
Compound 46 was synthesized from compound 45 as described for compound 38 to yield compound 46 as a beige solid. MS (ESI, EI+): m/z=643 (MH+).
Sources & evidence
- ORD record
- ord-7683bf7c47e74e59ab6340cfc5ad3f3d
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284307B2
Reaction notes
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