Trifluoroacetic acid → HCID 23523300, compound

HRID 392899Notes

Reaction equation

C([O:5][C:6](=[O:40])[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[CH:11][C:10]=1[CH2:16][NH:17][C:18]1[N:26]=[CH:25][N:24]=[C:23]2[C:19]=1[N:20]=[CH:21][N:22]2[C@H:27]1[C@H:31]([OH:32])[C@H:30]([N:33]=[N+:34]=[N-:35])[C@@H:29]([C:36](=[O:39])[NH:37][CH3:38])[O:28]1)(C)(C)C.FC(F)(F)C(O)=O>>[N:33]([C@@H:30]1[C@@H:29]([C:36](=[O:39])[NH:37][CH3:38])[O:28][C@@H:27]([N:22]2[CH:21]=[N:20][C:19]3[C:23]2=[N:24][CH:25]=[N:26][C:18]=3[NH:17][CH2:16][C:10]2[CH:11]=[C:12]([Cl:15])[CH:13]=[CH:14][C:9]=2[O:8][CH2:7][C:6]([OH:40])=[O:5])[C@@H:31]1[OH:32])=[N+:34]=[N-:35]

Participants

Reactant 2

HCID 6422Trifluoroacetic acid

HCID 86594475HCID 86594475, compound

Product 1

HCID 23523300HCID 23523300, compound

Procedure

(2R,3R,4S,5S)(2-{[9-(4-Azido-3-hydroxy-5-methylcarbamoyl-tetrahydro-furan-2-yl)-9H-purin-6-ylamino]-methyl}-4-chloro-phenoxy)-acetic acid tert-butyl ester (1 g, 1.9 mmol) was added to trifluoroacetic acid (15 mL) and stirred at room temperature for 3 hours. The mixture was concentrated and the residue was reconcentrated from chloroform three times to afford the title compound as a foam. M.S. 518 (M+H)+. 1H NMR (400 MHz, CD3OD) δ 8.5 (m, 2H); 7.38 (bs, 1H); 7.25 (d, 1H, J=8.0 Hz); 6.95 (d, 1H, J=8.0 Hz); 6.0 (d, 1H, J=4.0 Hz); 5.0 (m, 1H); 4.85 (m, 2H); 4.75 (s, 2H); 4.4 (m, 2H); 2.8 (s, 3H).

Workup

concentrationThe mixture was concentrated

Sources & evidence

ORD record: ord-e846c65f4b8f41078da48b76db2ede87
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06803457B1

Reaction notes

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