Lithium hydroxide, monohydrate → HCID 59269829, compound

HRID 1666973Notes

Reaction equation

HRID 1666973 reaction equation
[C:1]1([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:6]=[CH:5][C:4]([C@@:7]23[CH2:26][N:19]([C@H:20]([C:22]([O:24]C)=[O:23])[CH2:21]2)[C:18](=[O:27])[C@@H:17]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:16][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:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH:6]=[CH:5][C:4]([C@@:7]23[CH2:26][N:19]([C@H:20]([C:22]([OH:24])=[O:23])[CH2:21]2)[C:18](=[O:27])[C@@H:17]([NH:28][C:29]([O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[O:30])[CH2:16][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, monohydrateHCID 59269825HCID 59269825, compound

Product 1

HCID 59269829HCID 59269829, compoundYield 86%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (3S,13R,15S,E)-methyl 13-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)-2-oxo-12-thia-1-azabicyclo[11.2.1]hexadec-9-ene-15-carboxylate (90 mg, 0.156 mmol) in THF (1 mL) and MeOH (1.000 mL) was added pre-made solution of lithium hydroxide hydrate (19.58 mg, 0.467 mmol) in Water (1 mL). The resulting cloudy solution was stirred at room for 5 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,13R,15S,E)-13-(biphenyl-4-yl)-3-(tert-butoxycarbonylamino)-2-oxo-12-thia-1-azabicyclo[11.2.1]hexadec-9-ene-15-carboxylic acid (84 mg, 0.134 mmol, 86% yield) as an off-white foam. LC-MS (retention time: 3.32 min, method C), MS m/z 565 (M+H).

Workup

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

Sources & evidence

ORD record
ord-1a50a17bf9e34911b1d9827daf0aec71
Source dataset
uspto-grants-2011_10
Patent number
US08044087B2

Reaction notes

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