Diisopropylethylamine → 7-(4-(4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-hydroxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 1893867Notes

Reaction equation

HRID 1893867 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[CH2:21][C@H:20]([CH2:22][NH:23][C:24](=[O:26])[CH3:25])[O:19][C:18]2=[O:27])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1([OH:16])[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]1.C(OB(O)OC(=O)C)(=O)C.[CH:38]1([N:41]2[C:50]3[C:45](=[CH:46][C:47]([F:54])=[C:48](F)[C:49]=3[O:51][CH3:52])[C:44](=[O:55])[C:43]([C:56]([OH:58])=[O:57])=[CH:42]2)[CH2:40][CH2:39]1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[C:24]([NH:23][CH2:22][C@@H:20]1[O:19][C:18](=[O:27])[N:17]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]3([OH:16])[CH2:15][CH2:14][N:13]([C:48]4[C:49]([O:51][CH3:52])=[C:50]5[C:45]([C:44](=[O:55])[C:43]([C:56]([OH:58])=[O:57])=[CH:42][N:41]5[CH:38]5[CH2:40][CH2:39]5)=[CH:46][C:47]=4[F:54])[CH2:12][CH2:11]3)=[C:2]([F:1])[CH:3]=2)[CH2:21]1)(=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 11164924HCID 11164924, compoundHCID 67279369HCID 67279369, compound

Product 1

HCID 589162647-(4-(4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-4-hydroxy-piperidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

In analogy to example 76 with 114 mg N-[{(5S)-3[3-fluoro-4-(4-hydroxy-piperidin-4-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-yl-methyl}]-acetamide. (MW: 381.40 0.3 mmol), 127 mg of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid diacetylborate (Sakurai, Nobuhiro; Sano, Mitsuharu; Hirayama, Fumihiro; Kuroda, Tsuyoshi; Uemori, Satoru; Bioorg. Med. Chem. Lett.; 8; 16; 1998; 2185-2190) (MW: 423.137, 0.3 mmol) and 38 mg of ethyl diisopropylamine (MW: 129.25, 0.3 mmol) in 1 ml N-methyl-pyrrolidin-2-one. Yield: 137 mg, 69.5%. MS: 658.2 (M+H)+, 655.8 (M+H)−, Method ESI+, ESI−.

Sources & evidence

ORD record
ord-c0f50e864d304df3ac4d12f2792a8331
Source dataset
uspto-grants-2013_08
Patent number
US08513231B2

Reaction notes

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