(2S,3R,4R,5S)-2,4-bis(acetoxy)-5-(3-ethyl-1,2,4-oxadiazol-5-yl)tetrahydro-3-furanyl acetate → (2R,3R,4S,5S)-4-(Acetyloxy)-2-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulphonyl)amino]methyl}-9H-purin-9-yl)-5-(3-ethyl-1,2,4-oxadiazol-5-yl)tetrahydro-3-furanyl Acetate

HRID 1168302Notes

Reaction equation

HRID 1168302 reaction equation
Cl.[C:2]1([CH:8]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:9][NH:10][C:11]2[N:19]=[C:18]([CH2:20][NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:24])=[O:23])[N:17]=[C:16]3[C:12]=2[N:13]=[CH:14][NH:15]3)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:35]([O:38][C@@H:39]1[C@H:43]([O:44][C:45](=[O:47])[CH3:46])[C@@H:42]([C:48]2[O:52][N:51]=[C:50]([CH2:53][CH3:54])[N:49]=2)[O:41][C@@H:40]1OC(=O)C)(=[O:37])[CH3:36].C(O[C@@H]1[C@H](OC(=O)C)[C@@H](C2ON=C(CC)N=2)O[C@H]1OC(=O)C)(=O)C>>[C:35]([O:38][C@@H:39]1[C@H:43]([O:44][C:45](=[O:47])[CH3:46])[C@@H:42]([C:48]2[O:52][N:51]=[C:50]([CH2:53][CH3:54])[N:49]=2)[O:41][C@H:40]1[N:15]1[CH:14]=[N:13][C:12]2[C:16]1=[N:17][C:18]([CH2:20][NH:21][S:22]([CH2:25][CH:26]([CH3:28])[CH3:27])(=[O:23])=[O:24])=[N:19][C:11]=2[NH:10][CH2:9][CH:8]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)(=[O:37])[CH3:36]

Participants

4

Reactant 3

HCID 69976793(2S,3R,4R,5S)-2,4-bis(acetoxy)-5-(3-ethyl-1,2,4-oxadiazol-5-yl)tetrahydro-3-furanyl acetateHCID 69978211(2R,3R,4R,5S)-2,4-bis(acetoxy)-5-(3-ethyl-1,2,4-oxadiazol-5-yl)tetrahydro-3-furanyl acetateHCID 178455636HCID 178455636, compound

Product 1

HCID 59094538(2R,3R,4S,5S)-4-(Acetyloxy)-2-(6-[(2,2-diphenylethyl)amino]-2-{[(isobutylsulphonyl)amino]methyl}-9H-purin-9-yl)-5-(3-ethyl-1,2,4-oxadiazol-5-yl)tetrahydro-3-furanyl Acetate

Procedure

Prepared by the same method as Preparation 26 from N-({6-[(2,2-diphenylethyl)amino]-9H-purin-2-yl}methyl)-2-methyl-1-propanesulphonamide hydrochloride (Preparation 8) and a mixture of (2R,3R,4R,5S)-2,4-bis(acetoxy)-5-(3-ethyl-1,2,4-oxadiazol-5-yl)tetrahydro-3-furanyl acetate and (2S,3R,4R,5S)-2,4-bis(acetoxy)-5-(3-ethyl-1,2,4-oxadiazol-5-yl)tetrahydro-3-furanyl acetate (Preparation 14).

Sources & evidence

ORD record
ord-55dc3706c99440468092f5d68ebb8940
Source dataset
uspto-grants-2003_09
Patent number
US06624158B2

Reaction notes

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