2-((tert-Butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acid → Methyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[N-tert-butoxycarbonyl-beta-(3-chlorophenyl)-D,L-alanylamino]-beta-D-ribofuranuronate

HRID 1633308Notes

Reaction equation

HRID 1633308 reaction equation
[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([O:19][CH3:20])=[O:18])[C@@H:14]([NH2:21])[C@H:12]1[OH:13].[C:22]([O:26][C:27]([NH:29][CH:30]([C:39](O)=[O:40])[CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=1)=[O:28])([CH3:25])([CH3:24])[CH3:23]>>[NH2:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[C@@H:11]1[O:16][C@H:15]([C:17]([O:19][CH3:20])=[O:18])[C@@H:14]([NH:21][C:39](=[O:40])[CH:30]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[C:34]([Cl:38])[CH:33]=2)[NH:29][C:27]([O:26][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:28])[C@H:12]1[OH:13]

Participants

3

Reactant 2

HCID 69156842-((tert-Butoxycarbonyl)amino)-3-(3-chlorophenyl)propanoic acidHCID 54526695HCID 54526695, compound

Product 1

HCID 22828234Methyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[N-tert-butoxycarbonyl-beta-(3-chlorophenyl)-D,L-alanylamino]-beta-D-ribofuranuronateYield 54.2%

Procedure

Methyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-[N-tert-butoxycarbonyl-β-(3-chlorophenyl)-D,L-alanylamino]-β-D-ribofuranuronate (312 mg) was prepared by reacting methyl 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronate (294 mg) prepared in Example 62 with N-tert-butoxycarbonyl-β-(3-chlorophenyl)-D,L-alanine (300 mg) according to a similar manner to that of Example 64, mp. 115°-125° C.

Sources & evidence

ORD record
ord-554dcad4e03d4ab998069ffc54fa420e
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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