Lithium hydroxide, monohydrate → HCID 67444162, compound

HRID 1666980Notes

Reaction equation

HRID 1666980 reaction equation
[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:6]=[CH:5][C:4]([C@@:7]23[CH2:25][N:18]([C@H:19]([C:21]([O:23]C)=[O:22])[CH2:20]2)[C:17](=[O:26])[C@@H:16]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][S:8]3)=[CH:3][CH:2]=1.O.[OH-].[Li+]>C1COCC1.CO.O>[C:1]1([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:6]=[CH:5][C:4]([C@@:7]23[CH2:25][N:18]([C@H:19]([C:21]([OH:23])=[O:22])[CH2:20]2)[C:17](=[O:26])[C@@H:16]([NH:27][C:28]([O:30][C:31]([CH3:34])([CH3:32])[CH3:33])=[O:29])[CH2:15][CH2:14][CH2:13][CH2:12][CH:11]=[CH:10][CH2:9][S:8]3)=[CH:3][CH:2]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrate2×HCID 67444663HCID 67444663, compound

Product 1

HCID 67444162HCID 67444162, compoundYield 74.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,12R,14S,E)-methyl 12-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)-2-oxo-11-thia-1-azabicyclo[10.2.1]pentadec-8-ene-14-carboxylate (90 mg, 0.159 mmol) in THF (1 mL) and MeOH (1.000 mL) was added pre-made solution of lithium hydroxide hydrate (20.06 mg, 0.478 mmol) in Water (1 mL). The resulting cloudy solution was stirred at room for 15 h. LS/MS showed the reaction was only half way done. Another portion of lithium hydroxide hydrate (20.06 mg, 0.478 mmol) was added, and stirred for additional 20 h. Quenched with 5% citric acid, extracted with EtOAc. The organic layer was washed with brine, dried over MgSO4, filtered, evaporated, to afford the desired product (3S,12R,14S,E)-12-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)-2-oxo-11-thia-1-azabicyclo[10.2.1]pentadec-8-ene-14-carboxylic acid (72 mg, 0.118 mmol, 73.8% yield) as a white foam. LC-MS (retention time: 3.10 min, method C), MS m/z 551 (M+H).

Workup

  1. stirringstirred for additional 20 h
  2. customQuenched with 5% citric acid
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-028c055cf1a44bf69f9000254755ff36
Source dataset
uspto-grants-2011_10
Patent number
US08044087B2

Reaction notes

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