Hydrochloric Acid → HCID 54259323, compound

HRID 1955430Notes

Reaction equation

HRID 1955430 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][C@H:11]([CH2:13][S:14][C:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[O:10][C:9]1=[O:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[OH-:35].[Na+].Cl>CO.C1COCC1.O>[OH:35][C@@H:11]([CH2:13][S:14][C:15]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:12][C@@H:8]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7])[C:9]([OH:10])=[O:34]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 9826097HCID 9826097, compound

Product 1

HCID 54259323HCID 54259323, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 3.72 g (7.88 mmol) of the product of Example 17 in 10 mL of methanol/THF (1:1) at room temperature was added 16.7 mL of 1.0N NaOH solution. The reaction was stirred at room temperature for 1 h and then diluted with 100 mL of H2O and carefully acidified to pH 6 with 5% HCl solution. The resulting mixture was extracted with EtOAc and the combined organic layers were washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The residue, 3.72 g (100%) of the crude hydroxy-acid was used in the next step (Example 25) without further purification. Electrospray Mass Spec: 489.4 (M-H)-.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. washthe combined organic layers were washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue, 3.72 g (100%) of the crude hydroxy-acid was used in the next step (Example 25) without further purification

Sources & evidence

ORD record
ord-0d74a0735af34d9d9ea12a5d5d8454c6
Source dataset
uspto-grants-2000_09
Patent number
US06124502

Reaction notes

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