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

HRID 1893871Notes

Reaction equation

HRID 1893871 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:16]2[CH2:20][C@H:19]([CH2:21][NH:22][C:23](=[O:25])[CH3:24])[O:18][C:17]2=[O:26])[CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]1([OH:15])[CH2:14][CH2:13][NH:12][CH2:11]1.C(OB(O)OC(=O)C)(=O)C.[CH:37]1([N:40]2[C:49]3[C:44](=[CH:45][C:46]([F:53])=[C:47](F)[C:48]=3[O:50][CH3:51])[C:43](=[O:54])[C:42]([C:55]([OH:57])=[O:56])=[CH:41]2)[CH2:39][CH2:38]1.C(N(C(C)C)C(C)C)C>CN1CCCC1=O>[C:23]([NH:22][CH2:21][C@@H:19]1[O:18][C:17](=[O:26])[N:16]([C:4]2[CH:5]=[CH:6][C:7]([O:8][CH2:9][C:10]3([OH:15])[CH2:14][CH2:13][N:12]([C:47]4[C:48]([O:50][CH3:51])=[C:49]5[C:44]([C:43](=[O:54])[C:42]([C:55]([OH:57])=[O:56])=[CH:41][N:40]5[CH:37]5[CH2:39][CH2:38]5)=[CH:45][C:46]=4[F:53])[CH2:11]3)=[C:2]([F:1])[CH:3]=2)[CH2:20]1)(=[O:25])[CH3:24]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 57754804HCID 57754804, compoundHCID 67279369HCID 67279369, compound

Product 1

HCID 589162217-(3-{4-[(5S)-5-(Acetylamino-methyl)-2-oxo-oxazolidin-3-yl]-2-fluoro-phenoxymethyl}-3-hydroxy-pyrrolidin-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 143 mg N-{(5S)-3-[3-fluoro-4-(3-hydroxy-pyrrolidin-3-ylmethoxy)-phenyl]-2-oxo-oxazolidin-5-yl-methyl}-acetamide (MW: 367.38, 0.39 mmol), 165 mg of 1-cyclo-propyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinoline-carboxylic acid diacetylborate (MW: 423.137, 0.39 mmol) and 100 mg of ethyl diisopropylamine (MW: 129.25, 0.78 mmol) in 2 ml N-methyl-pyrrolidin-2-one. Yield: 143 mg, 57%. MS: 643.7 (M+H)+, 641.7 (M+H)−, Method ESI+, ESI−.

Sources & evidence

ORD record
ord-8d1e7d7a383b4534a8787944d01d5399
Source dataset
uspto-grants-2013_08
Patent number
US08513231B2

Reaction notes

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