(2R)-[(tert-Butoxycarbonyl)amino](cyclohexyl)acetic acid → [(R)-cyclohexyl-[3-(8-isopropyl-5-methyl-6-oxo-5,6,7,8-tetrahydro-pteridin-2-ylamino)-5-(methylsulfonyl)-phenylcarbamoyl]-methyl]-carbamic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:19][C:20]1[CH:21]=[C:22]([NH:30][C:31]2[N:40]=[CH:39][C:38]3[N:37]([CH3:41])[C:36](=[O:42])[CH2:35][N:34]([CH:43]([CH3:45])[CH3:44])[C:33]=3[N:32]=2)[CH:23]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:25]=1>>[C:1]([O:5][C:6](=[O:7])[NH:8][C@H:9]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)[C:10](=[O:12])[NH:19][C:20]1[CH:25]=[C:24]([S:26]([CH3:29])(=[O:27])=[O:28])[CH:23]=[C:22]([NH:30][C:31]2[N:40]=[CH:39][C:38]3[N:37]([CH3:41])[C:36](=[O:42])[CH2:35][N:34]([CH:43]([CH3:45])[CH3:44])[C:33]=3[N:32]=2)[CH:21]=1)([CH3:2])([CH3:3])[CH3:4]Participants
3
Reactant 2
Product 1
Procedure
Starting from (R)-tert-butoxycarbonylamino-cyclohexyl-acetic acid (31.6 mg; 0.123 mmol) and 2-(3-amino-5-(methylsulfonyl)-phenylamino)-8-isopropyl-5-methyl-7,8-dihydro-5H-pteridin-6-one (40 mg; 0.102), 11.3 mg (0.018 mmol; 17.5% yield) of the desired compound were obtained.
Sources & evidence
- ORD record
- ord-a6584675449e4f07a9f4632bb2791d35
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08410100B2
Reaction notes
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