Lithium hydroxide, monohydrate → HCID 42597521, compound

HRID 37772Notes

Reaction equation

HRID 37772 reaction equation
[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[C:18]3[C:23]([CH:24]=[C:25]4[C:30]=2[CH:29]=[CH:28][CH:27]=[CH:26]4)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][CH:12]=1)[C:6]([O:8]C)=[O:7])(=[O:3])[CH3:2].O.[OH-].[Li+]>C1COCC1.O.O>[C:1]([NH:4][C@@H:5]([CH2:10][C:11]1[CH:12]=[CH:13][C:14]([C:17]2[C:18]3[C:23]([CH:24]=[C:25]4[C:30]=2[CH:29]=[CH:28][CH:27]=[CH:26]4)=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:15][CH:16]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 42597519Methyl (2S)-2-acetamido-3-(4-[9-anthracenyl]phenyl)-propanoate

Product 1

HCID 42597521HCID 42597521, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 96 (80 mg, 0.20 mmol) in THF/water, 2:1 (3 mL) was added lithium hydroxide monohydrate (17 mg, 0.40 mmol) and the resulting suspension was allowed to stir for 16 h. The reaction mixture was diluted with water (30 mL) and the THF was removed by evaporation. The aqueous layer was washed with DCM (40 mL) to remove unreacted starting material. The aqueous phase was acidified with 10% HCl and the resulting precipitate was extracted with DCM (3×40 mL). The combined organics were dried and evaporated to yield the title compound (69 mg, 0.18 mmol, 90%) as a white solid. Mp 76° C. [α]D20 +29.7 (c. 0.1, EtOH). 1H NMR (CDCl3, 300 MHz): δ 8.47 (s, 1H, ArH10″); 8.02 (d, J=8.4 Hz, 2H, ArH3″ and ArH6″); 7.59 (d, J=8.7 Hz, 2H, ArH8″ and ArH1″); 7.45 (m, 2H, ArH4″ and ArH5″); 7.35 (m, 6H, ArH2″ and ArH7″, 4×ArH″); 6.27 (d, J=6.6 Hz, 1H, NH); 5.00 (m, 1H, H2); 3.39 (dd, J=4.8, 12.9 Hz, 1H, H3a); 3.26 (dd, J=6.3, 14.4 Hz, 1H, H3b); 2.07 (s, 3H, COCH3). Mass Spectrum (ES, +ve) m/z 383 (70%) [MH+]. HRMS calcd for C25H22NO3 384.1600, found 384.1610.

Workup

  1. customthe THF was removed by evaporation
  2. washThe aqueous layer was washed with DCM (40 mL)
  3. customto remove unreacted
  4. extractionthe resulting precipitate was extracted with DCM (3×40 mL)
  5. customThe combined organics were dried
  6. customevaporated

Sources & evidence

ORD record
ord-8278ed758fe04cd99037da7d467fc200
Source dataset
uspto-grants-2013_09
Patent number
US08524657B2

Reaction notes

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