Benzyl Alcohol → HCID 131723612, compound

HRID 993089Notes

Reaction equation

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

Participants

Reactant 2

HCID 244Benzyl Alcohol

HCID 22179287HCID 22179287, compound

Product 1

HCID 131723612HCID 131723612, compound

Procedure

According to the procedure described in Example 1, step 4, the phosphonic acid 43 was treated with benzyl alcohol. The ammonium salt was purified by flash chromatography (elution with chloroform:methanol:concentrated ammonium hydroxide; 8:2:0.25), followed by lyophilization, to afford the title compound: 1H NMR (300 MHz, D2O) δH 7.71 (m, 1H), 7.58 (m, 1H), 7.29 (s, 5H), 7.07 (t, J=7.0 Hz, 1H), 4.75 (d, J=7.8 Hz, 2H), 2.93 (d, J=12.9 Hz, 2H); 31P NMR: (121 MHz, D2O) δP 16.65; 13C NMR (75 MHz, D2O) δC 132.75; 131.1, 129.07, 128.72, 124.12, 123.70, 123.47, 123.13, 62.55, 34.40, (d, J=147.4 Hz).

Workup

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

Sources & evidence

ORD record: ord-2c320efd435a4e1f9ee95212c6d8c4ac
Source dataset: uspto-grants-2002_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06472406B1

Reaction notes

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