Trifluoroacetic acid → [4-(2-Amino-5-thiophen-2-yl-phenylcarbamoyl)-benzyl]-phosphonic acid monomethyl ester

HRID 1013462Notes

Reaction equation

[CH3:1][O:2][P:3]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14](=[O:28])[NH:15][C:16]2[CH:21]=[C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH:19]=[CH:18][C:17]=2[NH2:27])=[CH:10][CH:9]=1)(=[O:6])[O:4]C.[OH-].[Na+].C(O)(C(F)(F)F)=O>O1CCOCC1.CN(C=O)C>[CH3:1][O:2][P:3]([CH2:7][C:8]1[CH:9]=[CH:10][C:11]([C:14](=[O:28])[NH:15][C:16]2[CH:21]=[C:20]([C:22]3[S:23][CH:24]=[CH:25][CH:26]=3)[CH:19]=[CH:18][C:17]=2[NH2:27])=[CH:12][CH:13]=1)(=[O:4])[OH:6]

Participants

Conditions

Temperature: 80 °C

Procedure

[4-(2-Amino-5-thiophen-2-yl-phenylcarbamoyl)-benzyl]-phosphonic acid dimethyl ester (35 mg, 0.066 mmol) was made 0.25 M in dioxane and to this stirring solution was added 5N aqueous sodium hydroxide (26 μL, 0.132 mmol). The resulting solution was stirred at 80° C. overnight then diluted with DMF, acidified with TFA, and purified by HPLC (0-60% MeCN in water w/0.025% TFA) to afford the title compound: 1H NMR (DMSO-d6, 600 MHz) δ9.80 (s, 1H), 7.91 (d, J=8.4 Hz, 2H), 7.48-7.50 (m, 1H), 7.31-7.42 (m, 4H), 7.26-7.28 (m, 1H), 7.04-7.06 (m, 1H), 6.88 (d, J=8.4 Hz, 1H), 3.52 (d, J=11.4 Hz, 3H), 3.18 (d, J=21.6 Hz, 2H). MS: cal'd 403 (MH+), exp 403 (MH+)

Workup

custompurified by HPLC (0-60% MeCN in water w/0.025% TFA)

Sources & evidence

ORD record: ord-e786b246f1694051a501ad243e0c5adb
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07981874B2

Reaction notes

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