(2S)-5-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acid → (S)-4-Amino-4-(9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-ylcarbamoyl)butanoic acid hydrochloride

HRID 1912819Notes

Reaction equation

HRID 1912819 reaction equation
Cl.[NH2:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([C:29]([F:32])([F:31])[F:30])[CH:23]=2)=[O:20])=[CH:14][CH:13]=1.C([O:37][C:38](=[O:53])[CH2:39][CH2:40][C@@H:41]([C:50](O)=[O:51])[NH:42]C(OC(C)(C)C)=O)(C)(C)C>>[ClH:28].[NH2:42][C@H:41]([C:50](=[O:51])[NH:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[N:5]=[CH:6][N:7]2[C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][C:25]([Cl:28])=[C:24]([C:29]([F:31])([F:32])[F:30])[CH:23]=2)=[O:20])=[CH:16][CH:17]=1)[CH2:40][CH2:39][C:38]([OH:53])=[O:37]

Participants

3

Reactant 2

HCID 6993432(2S)-5-(tert-butoxy)-2-{[(tert-butoxy)carbonyl]amino}-5-oxopentanoic acidHCID 231551201-[4-(6-Aminopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea hydrochloride

Product 1

HCID 69315101(S)-4-Amino-4-(9-{4-[3-(4-chloro-3-(trifluoromethyl)phenyl)ureido]phenyl}-9H-purin-6-ylcarbamoyl)butanoic acid hydrochloride

Procedure

The title compound can be synthesized from 1-[4-(6-aminopurin-9-yl)phenyl]-3-(4-chloro-3-(trifluoromethyl)phenyl)urea hydrochloride and tert-butoxycarbonyl-L-glutamic acid 5-tert-butyl ester by using the same method as in Example 96.

Sources & evidence

ORD record
ord-7450c5c41d5f461ca2caeaa10e9c6031
Source dataset
uspto-grants-2013_12
Patent number
US08609656B2

Reaction notes

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