Benzyl Alcohol → HCID 131723612, compound

HRID 2109364Notes

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; 131.10, 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-a8aae8d12149427180eb65bf24cfb1ce
Source dataset: uspto-grants-2009_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07514556B2

Reaction notes

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