acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydro-furan-3-yl ester → acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethylamino)-2-chloro-purin-9-yl]-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydro-furan-3-yl ester

HRID 655122Notes

Reaction equation

Cl.[C:2]([O:5][C@@H:6]1[C@@H:10]([C:11]2ON=C(CC)C=2)[O:9][C@@H:8]([N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][C:21]([Cl:38])=[N:22][C:23]=3[NH:27][C@@H:28]([CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:29][OH:30])[C@@H:7]1[O:39][C:40](=[O:42])[CH3:41])(=[O:4])[CH3:3].C(O[C@@H]1[C@@H](C2[N:53]=[N:54][N:55]([CH2:57][CH3:58])[N:56]=2)O[C@@H](N2C=NC3C2=NC(Cl)=NC=3Cl)[C@@H]1OC(=O)C)(=O)C>>[C:2]([O:5][C@@H:6]1[C@@H:10]([C:11]2[N:53]=[N:54][N:55]([CH2:57][CH3:58])[N:56]=2)[O:9][C@@H:8]([N:18]2[CH:26]=[N:25][C:24]3[C:19]2=[N:20][C:21]([Cl:38])=[N:22][C:23]=3[NH:27][C@@H:28]([CH2:31][C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH2:29][OH:30])[C@@H:7]1[O:39][C:40](=[O:42])[CH3:41])(=[O:4])[CH3:3]

Participants

Reactant 2

HCID 12151756acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydro-furan-3-yl ester

HCID 86623488Acetic acid (2R,3R,4R,5S)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethyl amino)-2-chloro-purin-9-yl]-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester hydrochloride

Product 1

HCID 86623491acetic acid (2R,3R,4R,5R)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethylamino)-2-chloro-purin-9-yl]-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydro-furan-3-yl ester

Procedure

The title compound is prepared analogously to acetic acid (2R,3R,4R,5S)-4-acetoxy-2-[6-((S)-1-benzyl-2-hydroxy-ethyl amino)-2-chloro-purin-9-yl]5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester hydrochloride (Step CA1) by replacing acetic acid (2R,3R,4R,5S)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(3-ethyl-isoxazol-5-yl)-tetrahydro-furan-3-yl ester (WO 99/38877) with acetic acid (2R,3R,4R,5R)-4-acetoxy-2-(2,6-dichloro-purin-9-yl)-5-(2-ethyl-2H-tetrazol-5-yl)-tetrahydro-furan-3-yl ester (WO 98/28319).

Sources & evidence

ORD record: ord-a0a361ba8f06432391d7e8eec84c1f55
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08071565B2

Reaction notes

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