Hydrogen chloride-ethyl acetate → HCID 178439698, compound

HRID 1613509Notes

Reaction equation

HRID 1613509 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:44][CH2:45][CH3:46])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[C:33]([S:36][CH2:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=2)[NH: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].Cl.C(OCC)(=O)C>CO.C1COCC1.[OH-].[Li+]>[CH3:1][O:2][C:3]1[C:4]([CH2:44][CH2:45][CH3:46])=[C:5]([CH:28]=[CH:29][C:30]=1[C:31]1[N:32]=[C:33]([S:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[NH: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 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 178439699HCID 178439699, compound

Product 1

HCID 178439698HCID 178439698, compound

Reagents, catalysts & solvents 2

HCID 3939Lithium HydroxideSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The compound of Example 7 (12.0 mg, 18.6 μmol) in 1.0 ml of 4:1 methanol/THF and 40 ml of 1N lithium hydroxide was stirred at room temperature for 2.5 hours. The reaction mixture was poured into 0.5N hydrochloric acid/ethyl acetate. The ethyl acetate layer was washed with brine, dried over sodium sulfate, and concentrated under vacuum. Flash chromatography of the residue using 3:1 to 1:1 hexane/ethyl acetate (1% acetic acid) as eluant gave the product; melting point 92-97° C. High resolution mass spectrum, m/e 586.2868 (Calculated for C35H42O4N2S (M-CO2), 586.2865).

Workup

  1. washThe ethyl acetate layer was washed with brine
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customgave the product

Sources & evidence

ORD record
ord-d3d5a619e51d4b68984a711a70b54a95
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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