Benzoic acid 2-(4-benzoylamino-2-oxo-2H-pyridin-1-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl ester → {2-[5-(4-Amino-2-oxo-2H-pyridin-1-yl)-4-hydroxy-tetrahydro-furan-2-yl]-vinyl}-phosphonic acid

HRID 2191017Notes

Reaction equation

HRID 2191017 reaction equation
C([NH:9][C:10]1[CH:15]=[CH:14][N:13]([CH:16]2[CH:20]([O:21]C(=O)C3C=CC=CC=3)[CH2:19][CH:18]([CH:30]=[CH:31][P:32]([O:37]CC)([O:34]CC)=[O:33])[O:17]2)[C:12](=[O:40])[CH:11]=1)(=O)C1C=CC=CC=1.NC1NC(=O)C2N=NN(C3OC(C=CP(=O)(O)O)CC3O)C=2N=1>>[NH2:9][C:10]1[CH:15]=[CH:14][N:13]([CH:16]2[O:17][CH:18]([CH:30]=[CH:31][P:32](=[O:33])([OH:34])[OH:37])[CH2:19][CH:20]2[OH:21])[C:12](=[O:40])[CH:11]=1

Participants

3

Reactant 2

HCID 86641116Benzoic acid 2-(4-benzoylamino-2-oxo-2H-pyridin-1-yl)-5-[2-(diethoxy-phosphoryl)-vinyl]-tetrahydro-furan-3-yl esterHCID 136381448{2-[5-(5-Amino-7-oxo-6,7-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-3-yl)-4-hydroxy-tetrahydro-furan-2-yl]-vinyl}-phosphonic acid

Product 1

HCID 68593542{2-[5-(4-Amino-2-oxo-2H-pyridin-1-yl)-4-hydroxy-tetrahydro-furan-2-yl]-vinyl}-phosphonic acidYield 86.5%

Procedure

Compound 11.2 (97 mg, 86.5% yield) was synthesized from compound 11.1 (215 mg) using the procedure for the preparation of compound 10.2. 1H NMR (D2O) δ 1.8 (m, 1H), 2.05 (m, 1H), 4.3 (d, 1H, J=4.8), 4.8 (m, 1H), 5.69 (s, 1H), 6.0 (m, 1H), 6.2 (m, 1H), 7.52 (d, 1H, J=7.8). 31P NMR (D2O) d 9.8. LRMS (ESI) MH+ C10H14N3O6P requires 304.2. Found 304.0.

Sources & evidence

ORD record
ord-6fdfb5f99bb74421ba64240a54d6af31
Source dataset
uspto-grants-2012_12
Patent number
US08324179B2

Reaction notes

Loading…