Isopropyl chloroformate → (+/-)-cis-3-Methyl-4-[4-(2-methyl-benzoylamino)-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid isopropyl ester
Reaction equation
[C:1]([NH:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([S:20](Cl)(=[O:22])=[O:21])=[CH:12][CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:24][CH:25]1[CH2:30][CH2:29][N:28](CC2C=CC=CC=2)[CH2:27][CH:26]1[CH3:38].[C:39](OC(N1CCC(N)CC1)=O)(C)(C)C.Cl[C:54]([O:56][CH:57]([CH3:59])[CH3:58])=[O:55].N(C(C)C)=C=O>>[CH:57]([O:56][C:54]([N:28]1[CH2:29][CH2:30][C@H:25]([NH:24][S:20]([C:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[CH3:39])=[CH:11][CH:12]=2)(=[O:22])=[O:21])[C@H:26]([CH3:38])[CH2:27]1)=[O:55])([CH3:59])[CH3:58]Participants
6
Reactant 5
Product 1
Procedure
The title compounds were made following the general procedure in Scheme 5 and deprotection in Scheme 4-1, substituting 4-(2-methyl-benzoylamino)-naphthalene-1-sulfonyl chloride for 4-benzoylamino-naphthalene-1-sulfonyl chloride, (±)-4-amino-1-benzyl-3-methyl-piperidine for 4-amino-piperidine-1-carboxylic acid tert-butyl ester and isopropyl chloroformate for 2-isocyanato-propane. 1H NMR (300 MHz, CDCl3) δ 8.72 (d, 1H), 8.43 (d, 1H), 8.35 (d, 1H), 8.12 (d, 1H), 7.95 (d, 2H), 7.72 (m, 3H), 7.46 (m, 1H), 7.35 (d, 2H), 4.85 (m, 1H), 4.66 (d, 1H), 3.55 (m, 1H), 3.37 (m, 1H), 3.17 (m, 2H), 2.59 (s, 3H), 1.74 (m, 1H), 1.58 (m, 1H), 1.40 (m, 2H) 1.18 (dd, 6H), 0.67 (m, 3H); LC/MS m/z 524 (M+H)+.
Sources & evidence
- ORD record
- ord-803930af3e7e4c0ba76c1fed991a17b6
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08063222B2
Reaction notes
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