4-Nitrophenol → HCID 131723614, compound

HRID 1795774Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[S:6]([N:9]([CH2:11][P:12](=[O:15])([OH:14])[OH:13])[CH3:10])(=[O:8])=[O:7].[N+:16]([C:19]1[CH:24]=[CH:23][C:22](O)=[CH:21][CH:20]=1)([O-:18])=[O:17]>>[NH4+:9].[N+:16]([C:19]1[CH:24]=[CH:23][C:22]([O:15][P:12]([CH2:11][N:9]([S:6]([C:2]2[S:1][CH:5]=[CH:4][CH:3]=2)(=[O:7])=[O:8])[CH3:10])(=[O:13])[O-:14])=[CH:21][CH:20]=1)([O-:18])=[O:17]

Participants

Reactant 2

HCID 9804-Nitrophenol

HCID 22179271HCID 22179271, compound

Product 1

HCID 131723614HCID 131723614, compoundYield 43%

Procedure

Compound (xi) was treated with 4-nitrophenol according to the procedure described in Example 1, step 4. The crude product was purified by flash chromatography (elution with chloroform:methanol:concentrated ammonium hydroxide; 8:2:0.25) to afford the ammonium salt 47 (43%) as a colorless solid: 1H NMR (400 MHz, CD3OD) δH 8.19–8.23 (m, 2 H, Ar—H), 7.85 (dd, J=1, 5 Hz, 1 H, Ar—H), 7.62 (dd, J=1, 4 Hz, 1 H, Ar—H), 7.44 (dd, J=1, 9.5 Hz, 2 H, Ar—H), 7.23 (dd, J=4, 5 Hz, 1 H, Ar—H), 3.30 (d, J−13.5 Hz, 2 H, NCH2P), 2.93 (s, 3 H, NCH3); 13C NMR (100 MHz, CD3OD) δC 37.1, 47.4, 122.4 (d, J=4 Hz), 126.1, 128.9, 133.7 (d, J=7 Hz), 137.1, 144.7, 159.5; 31P NMR (162 MHz, CD3OD) δP 12.7; MS (neg. FAB) m/z 391 (M−1, 100%), 306 (15%), 153 (35%).

Workup

customThe crude product was purified by flash chromatography (elution with chloroform:methanol:concentrated ammonium hydroxide; 8:2:0.25)

Sources & evidence

ORD record: ord-eb9708404c8e478195c29d65f4127992
Source dataset: uspto-grants-2006_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07030103B2

Reaction notes

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