Lithium Hydroxide → (Z)-(1R,4R,6S,16R,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04.6]nonadec-7-ene-4-carboxylic acid

HRID 2242435Notes

Reaction equation

HRID 2242435 reaction equation
C([O:3][C:4]([C@@:6]12[CH2:24][C@H:23]1[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:14](=[O:33])[C@H:13]1[C@@H:9]([CH2:10][C@@H:11]([O:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=4)[N:38]=[C:37]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH:36]=3)[CH2:12]1)[C:8](=[O:53])[NH:7]2)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[C:29]([O:28][C:26]([NH:25][N:15]1[C:14](=[O:33])[C@H:13]2[C@@H:9]([CH2:10][C@@H:11]([O:34][C:35]3[C:44]4[C:39](=[CH:40][C:41]([O:45][CH3:46])=[CH:42][CH:43]=4)[N:38]=[C:37]([C:47]4[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=4)[CH:36]=3)[CH2:12]2)[C:8](=[O:53])[NH:7][C@@:6]2([C:4]([OH:5])=[O:3])[C@@H:23]([CH2:24]2)[CH:22]=[CH:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:27])([CH3:32])([CH3:30])[CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 11343098(Z)-(1R,4R,6S,16R,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04,6]nonadec-7-ene-4-carboxylic acid ethyl ester

Product 1

HCID 11320008(Z)-(1R,4R,6S,16R,18R)-14-tert-Butoxycarbonylamino-18-(7-methoxy-2-phenyl-quinolin-4-yloxy)-2,15-dioxo-3,14-diaza-tricyclo[14.3.0.04.6]nonadec-7-ene-4-carboxylic acidYield 46.4%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

To a solution of 49 (27 mg, 0.037 mmol) in THF/MeOH/H2O 2:1:1 (5 mL) was added 1 M LiOH (300 μL, 0.300 mmol). The solution was stirred for 24 h at room temperature and finally for one hour at reflux. After acidification to pH 3-4 with 1 M HCl and evaporation the residue was purified by HPLC (MeOH/H2O 80:20 and MeOH/H2O 90:10) providing 50 (12 mg, 46%) as a colorless solid.

Workup

  1. temperatureat reflux
  2. customAfter acidification to pH 3-4 with 1 M HCl and evaporation the residue
  3. customwas purified by HPLC (MeOH/H2O 80:20 and MeOH/H2O 90:10)

Sources & evidence

ORD record
ord-daac0596651c43d8b6bd0dd61ae1f53f
Source dataset
uspto-grants-2010_03
Patent number
US07671032B2

Reaction notes

Loading…