Lithium Hydroxide → HCID 24997808, compound

HRID 2201963Notes

Reaction equation

HRID 2201963 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[S:8][C:9]([CH2:12][CH2:13][CH2:14][C@H:15]2[CH2:19][CH2:18][CH:17]=[C:16]2[C:20]2[CH:25]=[CH:24][C:23]([C@@H:26]([OH:32])[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[CH:22][CH:21]=2)=[CH:10][CH:11]=1)=[O:6]>C1COCC1>[OH:32][C@H:26]([C:23]1[CH:24]=[CH:25][C:20]([C:16]2[C@@H:15]([CH2:14][CH2:13][CH2:12][C:9]3[S:8][C:7]([C:5]([OH:6])=[O:4])=[CH:11][CH:10]=3)[CH2:19][CH2:18][CH:17]=2)=[CH:21][CH:22]=1)[CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 24997809HCID 24997809, compound

Product 1

HCID 24997808HCID 24997808, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

LiOH (0.5 mL, 0.5 mmol, 1 M) was added to a THF (1.5 mL) solution of 43 (14 mg, 0.033 mmol). The mixture was stirred overnight at 60° C., allowed to cool to room temperature and then quenched by addition of 1 M HCl (10 mL). The mixture was extracted with CH2Cl2 (3×15 mL) and the combined CH2Cl2 solution was dried (Na2SO4), filtered and evaporated to leave the title compound (13 mg, 0.031 mmol, 95%).

Workup

  1. temperatureto cool to room temperature
  2. customquenched by addition of 1 M HCl (10 mL)
  3. extractionThe mixture was extracted with CH2Cl2 (3×15 mL)
  4. dry with materialthe combined CH2Cl2 solution was dried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-6155504abeac447380991042f63e20bd
Source dataset
uspto-grants-2016_06
Patent number
US09365485B2

Reaction notes

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