Ethanol → HCID 68501153, compound

HRID 1966492Notes

Reaction equation

HRID 1966492 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[N:30]=[C:31]4[C:36](=[C:37]5[C:42]=3[CH:41]=[CH:40][CH:39]=[CH:38]5)[CH:35]=[CH:34][CH:33]=[CH:32]4)[CH2:27][C@H:21]2[C:20](=[O:43])[NH:19][C@:18]2([C:45]([O:47]CC)=[O:46])[CH2:44][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)C.[OH-].[Li+]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]1[C:23](=[O:24])[N:22]2[CH2:25][C@H:26]([O:28][C:29]3[N:30]=[C:31]4[C:36](=[C:37]5[C:42]=3[CH:41]=[CH:40][CH:39]=[CH:38]5)[CH:35]=[CH:34][CH:33]=[CH:32]4)[CH2:27][C@H:21]2[C:20](=[O:43])[NH:19][C@:18]2([C:45]([OH:47])=[O:46])[CH2:44][C@H:17]2[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 68499992HCID 68499992, compound

Product 1

HCID 68501153HCID 68501153, compoundYield 100.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of the product of Example 24b (7.8 g, 11.6 mmol) in tetrahydrofuran (40 ml)/ethanol (40 ml) was added an aqueous lithium hydroxide solution (0.84 g of lithium hydroxide in 40 ml of H2O). The resulting mixture was heated to 50° C. for two hours and cooled to room temperature. The organic solvents were mostly removed under reduced pressure, and the resulting residue was acidified with 10% citric acid aqueous solution and extracted with ethyl acetate (200 ml). The organic layer was separated, washed with brine (200 ml), dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give a light yellow solid, which was further dried in a vacuum oven at 45° C. for 18 h to afford 7.5 g of product 24c as a light yellow solid; MS-DCI/NH3: 643 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customThe organic solvents were mostly removed under reduced pressure
  3. extractionextracted with ethyl acetate (200 ml)
  4. customThe organic layer was separated
  5. washwashed with brine (200 ml)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customto give a light yellow solid, which
  10. customwas further dried in a vacuum oven at 45° C. for 18 h

Sources & evidence

ORD record
ord-59df5779569b421b99febcef0065931e
Source dataset
uspto-grants-2013_04
Patent number
US08420596B2

Reaction notes

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