1-(6-Amino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-beta-(4-fluorophenyl)-D,L-alanylamino]-1,3-dideoxy-beta-D-ribofuranuronic acid → 3-[2-Amino-3-(4-fluorophenyl)propanoylamino]-5-(6-aminopurin-9-yl)-4-hydroxyoxolane-2-carboxylic acid

HRID 1633302Notes

Reaction equation

HRID 1633302 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]([OH:19])=[O:18])[C@@H:14]([NH:20][C:21](=[O:39])[CH:22]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[NH:23]C(OC(C)(C)C)=O)[C@H:12]1[OH:13]>C(O)=O>[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]([OH:19])=[O:18])[C@@H:14]([NH:20][C:21](=[O:39])[CH:22]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[NH2:23])[C@H:12]1[OH:13]

Participants

3

Reactant 1

HCID 228282231-(6-Amino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-beta-(4-fluorophenyl)-D,L-alanylamino]-1,3-dideoxy-beta-D-ribofuranuronic acid

Product 1

HCID 4761033-[2-Amino-3-(4-fluorophenyl)propanoylamino]-5-(6-aminopurin-9-yl)-4-hydroxyoxolane-2-carboxylic acidYield 66.2%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

1-(6-Amino-9H-purin-9-yl)-3-[β-(4-fluorophenyl)-D,L-alanylamino]-1,3-dideoxy-β-D-ribofuranuronic acid (173 mg) was prepared by reacting 1-(6-amino-9H-purin-9-yl)-3-[N-tert-butoxycarbonyl-β-(4-fluorophenyl)-D,L-alanylamino]-1,3-dideoxy-β-D-ribofuranuronic acid (320 mg) prepared in Example 27 and formic acid (5 ml) according to a similar manner to that of Example 45, mp. 120°-130° C. (dec.).

Sources & evidence

ORD record
ord-04d3e3a93f9342728a63bd745da05d71
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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