Lithium Hydroxide → HCID 67971935, compound

HRID 1804582Notes

Reaction equation

HRID 1804582 reaction equation
[Si:1]([O:8][C@H:9]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C@H:10]1[CH2:14][CH2:13][C@@H:12]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]([O:24]C)=[O:23])=[CH:18][CH:17]=2)[N:11]1[C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[Li+].[OH-]>CO>[C:29]([O:28][C:26]([N:11]1[C@@H:10]([C@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:5])[CH3:7])([CH3:3])[CH3:2])[C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH2:14][CH2:13][C@H:12]1[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]([OH:24])=[O:23])=[CH:20][CH:21]=1)=[O:27])([CH3:30])([CH3:31])[CH3:32]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 86666751HCID 86666751, compound

Product 1

HCID 67971935HCID 67971935, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of the title compound from Step E (800 mg, 1.48 mmol) in MeOH (7.5 ml) was added 1 N LiOH (7.41 ml, 7.41 mmol) and the mixture was stirred at RT overnight. LC-MS showed no more starting material left. The mixture was evaporated to remove MeOH, extracted the aqueous layer with ether 3×50 ml, the aqueous layer was adjusted to PH=4.5 with 1N HCl, then extracted with ethyl acetate 3×50 ml. The combined organic layers was washed with brine (saturated, 1×50 mL), dried (Na2SO4), filtered and the solvent evaporated under reduced pressure to afford title compound (i-5). Yield is 99%. LC-MS: m/z (E/S) 526.2 (MH)+.

Workup

  1. waitleft
  2. customThe mixture was evaporated
  3. customto remove MeOH
  4. extractionextracted the aqueous layer with ether 3×50 ml
  5. extractionextracted with ethyl acetate 3×50 ml
  6. washThe combined organic layers was washed with brine (saturated, 1×50 mL)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-0befaea039af4da787ad0c7cd330d2bd
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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