2-((tert-Butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoic acid → 1-(6-Benzoylamino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-beta-(4-fluorophenyl)-D,L-alanylamino]-1,3-dideoxy-beta-D-ribofuranuronic acid

HRID 1633279Notes

Reaction equation

HRID 1633279 reaction equation
[NH2:1][C@@H:2]1[C@@H:6]([C:7]([OH:9])=[O:8])[O:5][C@@H:4]([N:10]2[CH:18]=[N:17][C:16]3[C:11]2=[N:12][CH:13]=[N:14][C:15]=3[NH:19][C:20](=[O:27])[C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C@@H:3]1[OH:28].[C:29]([O:33][C:34]([NH:36][CH:37]([C:46](O)=[O:47])[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([F:45])=[CH:41][CH:40]=1)=[O:35])([CH3:32])([CH3:31])[CH3:30]>>[C:20]([NH:19][C:15]1[N:14]=[CH:13][N:12]=[C:11]2[C:16]=1[N:17]=[CH:18][N:10]2[C@@H:4]1[O:5][C@H:6]([C:7]([OH:9])=[O:8])[C@@H:2]([NH:1][C:46](=[O:47])[CH:37]([CH2:38][C:39]2[CH:40]=[CH:41][C:42]([F:45])=[CH:43][CH:44]=2)[NH:36][C:34]([O:33][C:29]([CH3:32])([CH3:30])[CH3:31])=[O:35])[C@H:3]1[OH:28])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 27567942-((tert-Butoxycarbonyl)amino)-3-(4-fluorophenyl)propanoic acidHCID 538540083-amino-1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 228282261-(6-Benzoylamino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-beta-(4-fluorophenyl)-D,L-alanylamino]-1,3-dideoxy-beta-D-ribofuranuronic acidYield 88.6%

Procedure

1-(6-Benzoylamino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-β-(4-fluorophenyl)-D,L-alanylamino]-1,3-dideoxy-β-D-ribofuranuronic acid (575 mg) was prepared by reacting 1-(6-benzoylamino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid (384 mg) prepared in Example 1 with N-hydroxysuccinimide ester of N-tert-butoxycarbonyl-β-(4-fluorophenyl)-D,L-alanine (417 mg) according to a similar manner to that of Example 5, mp. 125°-134° C. (dec.).

Sources & evidence

ORD record
ord-a4be331eb3924bcaa1d9aae245211d14
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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