Bis(p-nitrophenyl)-phosphate → HCID 72326310, compound

HRID 1175667Notes

Reaction equation

C(O[CH:5]1[CH:9]([O:10][C:11](=[O:18])[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:8][CH:7]([O:19][CH2:20][P:21]([O:26][CH2:27][CH3:28])([O:23][CH2:24][CH3:25])=[O:22])[O:6]1)(=O)C.[CH3:29][O:30][C:31]([C:33]1[N:37]=[CH:36][NH:35][N:34]=1)=[O:32].[N+](C1C=CC(OP([O-])(OC2C=CC([N+]([O-])=O)=CC=2)=O)=CC=1)([O-])=O>>[CH3:29][O:30][C:31]([C:33]1[N:37]=[CH:36][N:35]([CH:5]2[CH:9]([O:10][C:11](=[O:18])[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:8][CH:7]([O:19][CH2:20][P:21]([O:23][CH2:24][CH3:25])([O:26][CH2:27][CH3:28])=[O:22])[O:6]2)[N:34]=1)=[O:32]

Participants

Reactant 3

HCID 5255575Bis(p-nitrophenyl)-phosphate

HCID 72233966HCID 72233966, compound

HCID 178499122HCID 178499122, compound

Product 1

HCID 72326310HCID 72326310, compoundYield 65%

Procedure

Benzoic acid 2-acetoxy-5-(diethoxy-phosphorylmethoxy)-tetrahydro-furan-3-yl ester (170 mg, 0.4 mmol), 1H-[1,2,4]Triazole-3-carboxylic acid methyl ester (51 mg, 0.4 mmol) and Bis-(p-nitrophenyl)phosphate were reacted according to literature procedure (J. Med. Chem. 2000, 43, 1019-1028). The desired product was isolated in 65% yield (150 mg). 1H NMR (CDCl3, 300 MHz) δ 8.60 (s, 1H), 8.00 (d, 2H, J=7.8 Hz), 7.60 (t, 1H, J=7.2 Hz), 7.45 (app t, 2H, J=7.7 Hz), 6.29 (d, 1H, J=1.5 Hz), 5.91-5.98 (m, 1H), 5.67-5.71 (m, 1H), 4.11-4.23 (m, 4H), 3.96-4.04 (m, 4H), 3.85-3.92 (m, 1H), 2.55-2.72 (m, 2H), 1.29-1.37 (m, 6H). 31P NMR (121.4 MHz, CDCl3) δ 19.8. LRMS (ESI) MH+ C20H27N3O9P requires 484.1 Found 483.8.

Sources & evidence

ORD record: ord-e95b71f088e74196ad5819535cf0860e
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842672B2

Reaction notes

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