Lithium hydroxide, monohydrate → HCID 118194678, compound

HRID 1770375Notes

Reaction equation

HRID 1770375 reaction equation
[CH2:1]([O:8][C@H:9]([C@H:26]([C@@H:32]([OH:34])[CH3:33])[CH2:27][CH2:28][CH:29]([CH3:31])[CH3:30])[CH2:10][CH2:11][CH2:12][C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:14]([O:16]C)=[O:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O[Li].O>C1COCC1.O.CCOC(C)=O.Cl>[CH2:1]([O:8][C@H:9]([C@H:26]([C@@H:32]([OH:34])[CH3:33])[CH2:27][CH2:28][CH:29]([CH3:30])[CH3:31])[CH2:10][CH2:11][CH2:12][C@H:13]([NH:18][C:19]([O:21][C:22]([CH3:23])([CH3:25])[CH3:24])=[O:20])[C:14]([OH:16])=[O:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118194697HCID 118194697, compound

Product 1

HCID 118194678HCID 118194678, compoundYield 88.3%

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2S,6S,7S)-methyl 6-(benzyloxy)-2-((tert-butoxycarbonyl)amino)-7-((S)-1-hydroxyethyl)-10-methylundecanoate (700 mg, 1.46 mmol) in THF (9.73 mL) and H2O (4.87 mL) was added LiOH.H2O (184 mg, 4.38 mmol), and the reaction was stirred at room temperature for 4 h. The reaction was diluted with EtOAc (15 mL) and 0.2 M HCl (15 mL), the phases were separated, and the aq. phase was further extracted with EtOAc (3×15 mL). The combined organic extracts were washed with brine (8 mL), dried over Na2SO4, filtered, and concentrated to dryness to afford the title compound (600 mg, 1.289 mmol, 88%) as a white solid: 1H NMR (400 MHz, CDCl3) δ 7.31-7.21 (m, 5H), 5.63 (s, 1H), 4.57-4.45 (m, 2H), 3.89-3.74 (m, 2H), 3.59-3.52 (m, 1H), 1.92-1.63 (m, 2H), 1.63-0.94 (m, 22H), 0.83 (app dd, J=6.6, 2.1 Hz, 6H) (carboxylic acid and alcohol peaks are very broad (not listed)); 13C NMR (101 MHz, CDCl3) δ 179.67, 156.76, 138.11, 128.33, 128.05, 127.64, 80.99, 79.27, 71.52, 68.79, 56.30, 46.67, 37.81, 32.72, 29.56, 28.48, 28.27, 25.15, 23.19, 22.63, 22.50, 22.21; ESIMS m/z 464 ([M−H]−).

Workup

  1. customthe phases were separated
  2. extractionthe aq. phase was further extracted with EtOAc (3×15 mL)
  3. washThe combined organic extracts were washed with brine (8 mL)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-5a668e43262a4a5f96557b0185f61313
Source dataset
uspto-grants-2016_02
Patent number
US09247741B2

Reaction notes

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