Potassium Hydroxide → HCID 68751172, compound

HRID 1047125Notes

Reaction equation

HRID 1047125 reaction equation
[CH2:1]([O:8][P:9]([O:12][CH2:13][C@@H:14]([N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29]3[CH:30]=[N:31][C:32]([NH:44][C:45](=[O:49])[NH:46][CH2:47][CH3:48])=[CH:33][C:34]=3[C:35]3[S:36][CH:37]=[C:38]([C:40]([F:43])([F:42])[F:41])[N:39]=3)=[CH:26][N:27]=2)[C:22](=[O:50])[C:21]([C:51]([O:53]CC)=[O:52])=[CH:20]1)[CH2:15][CH:16]([CH3:18])[CH3:17])([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C>[CH2:1]([O:8][P:9]([O:12][CH2:13][C@@H:14]([N:19]1[C:28]2[C:23](=[CH:24][C:25]([C:29]3[CH:30]=[N:31][C:32]([NH:44][C:45](=[O:49])[NH:46][CH2:47][CH3:48])=[CH:33][C:34]=3[C:35]3[S:36][CH:37]=[C:38]([C:40]([F:41])([F:43])[F:42])[N:39]=3)=[CH:26][N:27]=2)[C:22](=[O:50])[C:21]([C:51]([OH:53])=[O:52])=[CH:20]1)[CH2:15][CH:16]([CH3:17])[CH3:18])([OH:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 68747842HCID 68747842, compound

Product 1

HCID 68751172HCID 68751172, compoundYield 37.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
62.5 °C

Procedure

To a stirred suspension of ethyl 1-[(2S)-1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (Example 23, 330 mg, 0.41 mmol) in ethanol (20 mL) was added 10% potassium hydroxide (69 mg, 1.23 mmol). The reaction mixture was heated to 60-65° C. overnight. The reaction mixture was cooled and then washed with ethyl acetate (20 mL). The pH of the aqueous layer was adjusted to 4 with dilute hydrochloric acid (2N) solution to give a solid precipitate which was filtered and dried to afford 120 mg (30%) of 1-[(2S)-1-{[(benzyloxy)(hydroxy)phosphoryl]oxy}-4-methylpentan-2-yl]-6-{6-[(ethylcarbamoyl)amino]-4-[4-(trifluoromethyl)-1,3-thiazol-2-yl]pyridin-3-yl}-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with ethyl acetate (20 mL)
  3. customto give a solid precipitate which
  4. filtrationwas filtered
  5. customdried

Sources & evidence

ORD record
ord-8bd467fccdfa4a2ca731ab8f86269b88
Source dataset
uspto-grants-2013_10
Patent number
US08569484B2

Reaction notes

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