Ethyl Acetate → HCID 10052575, compound

HRID 1461156Notes

Reaction equation

HRID 1461156 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH2:37][CH3:38])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[CH:33][S:34][CH:35]=1)[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]2[CH2:15][CH2:16][CH:17]([C:19]([O:21]C)=[O:20])[O:18][C:13]=2[C:12]=1[CH2:25][CH2:26][CH3:27].CO.C1COCC1.C(OCC)(=O)C>[OH-].[Li+]>[CH3:1][O:2][C:3]1[C:4]([CH2:36][CH2:37][CH3:38])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[CH:33][S:34][CH:35]=1)[O:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:24]=[CH:23][C:14]2[CH2:15][CH2:16][CH:17]([C:19]([OH:21])=[O:20])[O:18][C:13]=2[C:12]=1[CH2:25][CH2:26][CH3:27]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10075956HCID 10075956, compoundHCID 21899815MeOH tetrahydrofuran

Product 1

HCID 10052575HCID 10052575, compound

Reagents, catalysts & solvents 1

HCID 3939Lithium HydroxideSolvent2×

Procedure

The compound of Example 11 (27 mg, 50 mmol) was combined with 2 mL of 4:1 methanol/THF and 0.1 mL of IN lithium hydroxide, and the mixture was allowed to react at room temperature for 3 hr (another 0.05 mL LiOH was added after 1.5 hr). The reaction mixture was poured into ethyl acetate/0.5 M hydrochloric acid, and the ethyl acetate layer was washed with brine, dried over sodium sulfate and concentrated under vacuum to give the product. High resolution mass spectrum, m/e 481.2281 (calculated for C28H35SO4N (M-CO2), 481.2287).

Workup

  1. additionwas added after 1.5 hr)
  2. washthe ethyl acetate layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto give the product

Sources & evidence

ORD record
ord-ab8470a32b844aec8d45a7a783c09f9f
Source dataset
uspto-grants-1991_12
Patent number
US05073562

Reaction notes

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