N-Formyl-L-phenylalanine → (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-[[(2S)-2-formamido-3-phenyl-propanoyl]amino]-4-hydroxy-tetrahydrofuran-2-carboxylic acid

HRID 1633289Notes

Reaction equation

HRID 1633289 reaction equation
O.[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@@H:12]1[O:17][C@H:16]([C:18]([OH:20])=[O:19])[C@@H:15]([NH2:21])[C@H:13]1[OH:14].[CH:22]([NH:24][C@H:25]([C:33](O)=[O:34])[CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)=[O:23]>>[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@@H:12]1[O:17][C@H:16]([C:18]([OH:20])=[O:19])[C@@H:15]([NH:21][C:33](=[O:34])[C@H:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[NH:24][CH:22]=[O:23])[C@H:13]1[OH:14]

Participants

3

Reactant 2

HCID 759256N-Formyl-L-phenylalanineHCID 704655221-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-beta-D-ribofuranuronic acid monohydrate

Product 1

HCID 476106(2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-[[(2S)-2-formamido-3-phenyl-propanoyl]amino]-4-hydroxy-tetrahydrofuran-2-carboxylic acidYield 27.1%

Procedure

1-(6-Amino-9H-purin-9-yl)-1,3-dideoxy-3-(N-formyl-L-phenylalanylamino)-β-D-ribofuranuronic acid (58 mg) was prepared by reacting 1-(6-amino-9H-purin-9-yl)-1,3-dideoxy-3-amino-β-D-ribofuranuronic acid monohydrate (140 mg) prepared in Example 99 with N-hydroxysuccinimide ester of N-formyl-L-phenylalanine (130 mg) according to a similar manner to that of Example 5, mp. 169°-181° C. (dec.).

Sources & evidence

ORD record
ord-ea64af9a316f42ea8c11911fd6d7df00
Source dataset
uspto-grants-1984_10
Patent number
US04479942

Reaction notes

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