Lithium hydroxide, monohydrate → HCID 70874583, compound

HRID 1844748Notes

Reaction equation

HRID 1844748 reaction equation
[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH:16]=[C:15]([C:23]([CH3:26])([CH3:25])[CH3:24])[CH:14]=3)=[CH:11][C:10]([S:27]([NH:30][CH2:31][CH2:32][C:33]([O:35]C)=[O:34])(=[O:29])=[O:28])=[C:9]2[CH3:37])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O[Li].O>CO.O>[CH:1]1([CH2:7][N:8]2[C:12]([C:13]3[CH:18]=[C:17]([C:19]([CH3:21])([CH3:20])[CH3:22])[CH:16]=[C:15]([C:23]([CH3:25])([CH3:26])[CH3:24])[CH:14]=3)=[CH:11][C:10]([S:27]([NH:30][CH2:31][CH2:32][C:33]([OH:35])=[O:34])(=[O:28])=[O:29])=[C:9]2[CH3:37])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 70874528HCID 70874528, compound

Product 1

HCID 70874583HCID 70874583, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of compound 38 (400 mg, 0.75 mmol) in a mixture of MeOH (10 mL) and water (3 mL) was added LiOH.H2O (200 mg, 4.60 mmol) and then this mixture was stirred at 60° C. for 4 h, evaporated and acidified to pH˜5 with 3N HCl. The aq. layer was extracted with EA (3×). The combined organic layers were concentrated and purified by CC (PE/EA=2/1) to give compound 39 (345 mg, 79%) as a colorless oil. 1H-NMR (CDCl3, 300 MHz) δ: 0.60-0.66 (2H, m), 0.93-1.02 (3H, m), 1.23-1.38 (3H, m), 1.34 (18H, s), 1.51-1.55 (3H, m), 2.51 (3H, s), 2.64 (2H, t, J=5.4 Hz), 3.23-3.29 (2H, m), 3.70 (2H, d, J=7.2 Hz), 5.45 (1H, m), 6.42 (1H, s), 7.14 (2H, s), 7.40 (1H, s). MS Calcd.: 516; MS Found: 517 (M+1).

Workup

  1. customevaporated
  2. extractionThe aq. layer was extracted with EA (3×)
  3. concentrationThe combined organic layers were concentrated
  4. custompurified by CC (PE/EA=2/1)

Sources & evidence

ORD record
ord-e7aaba2e6d794c45bdc59990a9788db5
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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