Hydrochloric Acid → HCID 86687116, compound

HRID 1402274Notes

Reaction equation

HRID 1402274 reaction equation
C[O:2][C:3]([C@:5]1([CH2:11][O:12][Si:13]([CH:20]([CH3:22])[CH3:21])([CH:17]([CH3:19])[CH3:18])[CH:14]([CH3:16])[CH3:15])[CH2:9][CH2:8][CH2:7][N:6]1[CH3:10])=[O:4].O.[OH-].[Li+].Cl>CO.O>[CH3:10][N:6]1[CH2:7][CH2:8][CH2:9][C@@:5]1([CH2:11][O:12][Si:13]([CH:17]([CH3:19])[CH3:18])([CH:14]([CH3:16])[CH3:15])[CH:20]([CH3:22])[CH3:21])[C:3]([OH:4])=[O:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 86687115HCID 86687115, compound

Product 1

HCID 86687116HCID 86687116, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of Intermediate 85f (2.50 g, 7.93 mmol) and lithium hydroxide monohydrate (3.33 g, 79.3 mmol) in MeOH and water (50 mL) was stirred at reflux for 2 h. The cooled solution was acidified with 1M HCl to pH 5. The MeOH was removed in vacuo and the resulting aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried (MgSO4) and concentrated in vacuo to give the title compound as a white foam (2.21 g, 92%). 1H NMR (400 MHz, CDCl3): 1.00-1.21 (21H, m), 1.93-2.04 (2H, m), 2.32-2.42 (1H, m), 2.43-2.56 (1H, m), 2.96-3.09 (4H, m), 3.90-4.00 (1H, m), 4.20 (1H, d, J 10.9), 4.22 (1H, d, J 10.9).

Workup

  1. temperatureat reflux for 2 h
  2. customThe MeOH was removed in vacuo
  3. extractionthe resulting aqueous layer was extracted with EtOAc (3×)
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6cb4fa6169f94497a5bd64c7f9e4dfbd
Source dataset
uspto-grants-2014_12
Patent number
US08907094B2

Reaction notes

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