Trifluoroacetic acid → Methanol trifluoroacetic acid

HRID 405098ノート

反応式

HRID 405098 の反応式
[C:1](CCC(NC[C@]12CC[C@@H](C(C)=C)[C@@H]1[C@@H]1[C@@](C)(CC2)[C@@]2(C)[C@@H]([C@]3(C)[C@@H](CC2)C(C)(C)C(C2C=CC(C(O)=O)=CC=2)=CC3)CC1)=O)(O)=[O:2].[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49]>CO>[C:48]([OH:54])([C:50]([F:53])([F:52])[F:51])=[O:49].[CH3:1][OH:2]

参加物

4

反応物 2

HCID 6422Trifluoroacetic acidHCID 715967764-[(1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-[[(4-hydroxy-4-oxo-butanoyl)amino]methyl]-1-isopropenyl-5a,5b,8,8,11a-pentamethyl-1,2,3,4,5,6,7,7a,11,11b,12,13,13a,13b-tetradecahydrocyclopenta[a]chrysen-9-yl]benzoic acid

生成物 1

HCID 86669916Methanol trifluoroacetic acid

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((3-carboxypropanamido)methyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)benzoic acid (20 mg, 0.037 mmol) in methanol (2 ml) was added TFA to form a 0.1% v/v TFA-methanol solution. The mixture was stirred at rt for 28 h. The solvent was removed in vacuo and the resulting residue was purified by prep. HPLC. The product was isolated as a white solid (1.1 mg, 4.55%). LCMS: m/e 658.5 (MH+), 2.90 min (method 3). 1H NMR (400 MHz, MeOD) δ ppm 7.94 (d, J=8.5 Hz, 2H), 7.16-7.34 (m, 2H), 5.32 (dd, J=6.4, 1.6 Hz, 1H), 4.74 (d, J=2.0 Hz, 1H), 4.62 (s, 1H), 3.68 (s, 3H), 3.54 (d, J=13.6 Hz, 1H), 3.04 (d, J=13.8 Hz, 1H), 2.57-2.71 (m, 2H), 2.44-2.57 (m, 2H), 2.17 (dd, J=17.2, 6.4 Hz, 1H), 2.09 (dd, J=13.1, 1.8 Hz, 1H), 1.85 (dd, J=12.2, 3.4 Hz, 2H), 1.65-1.82 (m, 8H), 1.61 (br. s., 2H), 1.53 (d, J=10.5 Hz, 3H), 1.48 (d, J=2.0 Hz, 1H), 1.35-1.45 (m, 3H), 1.24-1.35 (m, 3H), 1.16-1.24 (m, 4H), 1.02-1.16 (m, 8H), 0.99 (s, 3H), 0.95 (s, 3H).

出典と根拠

ORDレコード
ord-34a4776e4764497a99f04343d35e52b4
出典データセット
uspto-grants-2014_06
特許番号
US08748415B2

反応ノート

読み込み中…