Gamma-Aminobutyric Acid → HCID 86748632, compound
Reaction equation
[C@@H:1]1([N:9]2[CH:16]=[CH:15][C:13]([NH2:14])=[N:12][C:10]2=[O:11])[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]1.S(=O)(O)[O-].[Na+].NCCCC(O)=O.C(CCCNC1C=CN([C@@H]2O[C@H](CO)[C@@H](O)C2)C(=O)N=1)(O)=O.[C@@H]1(N2C=CC(=O)NC2=O)O[C@H](CO)[C@@H](O)C1.NCCCCN.NCCCC.N[C:79]1[CH:80]=[C:81]([CH:85]=[CH:86][CH:87]=1)[C:82]([OH:84])=[O:83]>>[C:82]([C:81]1[CH:80]=[C:79]([NH:14][C:13]2[CH:15]=[CH:16][N:9]([C@@H:1]3[O:8][C@H:5]([CH2:6][OH:7])[C@@H:3]([OH:4])[CH2:2]3)[C:10](=[O:11])[N:12]=2)[CH:87]=[CH:86][CH:85]=1)([OH:84])=[O:83]Participants
Procedure
Efficient transamination of deoxycytidine is shown to have occurred when the reaction was carried out in the presence of 1M sodium bisulfite and 3M amine at pH 7.2 at a temperature of 48° C. While these conditions can be varied, it is noted that under the conditions used, the nucleoside was converted to 90% or greater of the transaminated product as determined by HPLC analysis. For example, transamination by 4-aminobutyric acid gave 93% of N4 -(3-carboxypropyl)deoxycytidine, 6% deoxyuridine and 1% deoxycytidine. Similar results were obtained when transamination was carried out with 1,4-diaminobutane or 1-aminobutane. Less efficient transamination was observed with 3-aminobenzoic acid, which gave N4 -(3-carboxyphenyl)deoxycytidine in approximately 30%. In this case, the lower extent of reaction appears to be due to the bulky nature of the amine and the lower solubility of the amine which only allowed a 1M solution to be prepared.
Workup
- customSimilar results
- customwere obtained when transamination
Sources & evidence
- ORD record
- ord-2864141cf2394b6db70c22e1b969c7c3
- Source dataset
- uspto-grants-1995_04
- Patent number
- US05407801
Reaction notes
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