Hydrochloric Acid → HCID 59465583, compound

HRID 2425063Notes

Reaction equation

HRID 2425063 reaction equation
[Li+].[OH-].C[O:4][C:5](=[O:32])[CH2:6][CH2:7][CH2:8]/[CH:9]=[CH:10]\[CH2:11][C@H:12]1[C:16](=[O:17])[CH2:15][CH2:14][C@@H:13]1[C:18]1[CH:23]=[CH:22][C:21]([CH:24]([CH:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[OH:25])=[CH:20][CH:19]=1.Cl>C1COCC1>[CH:26]1([CH:24]([OH:25])[C:21]2[CH:20]=[CH:19][C:18]([C@H:13]3[CH2:14][CH2:15][C:16](=[O:17])[C@@H:12]3[CH2:11]/[CH:10]=[CH:9]\[CH2:8][CH2:7][CH2:6][C:5]([OH:32])=[O:4])=[CH:23][CH:22]=2)[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59465585HCID 59465585, compound

Product 1

HCID 59465583HCID 59465583, compoundYield 102.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

LiOH (1 mL, 1 mmol, 1 M) was added to a solution of 4 (43 mg, 0.10 mmol) in THF (5.5 mL). The mixture was stirred overnight and then 1 M HCl was added. The resulting mixture was extracted with dichloromethane (3×25 mL) and the combined organic solution was dried (Na2SO4), filtered and evaporated. Flash chromatography on silica gel (3% methanol/dichloromethane) gave 5 (41 mg, 100%).

Workup

  1. extractionThe resulting mixture was extracted with dichloromethane (3×25 mL)
  2. dry with materialthe combined organic solution was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-f096ecb01dda434b94c32fe8beef926e
Source dataset
uspto-grants-2011_06
Patent number
US07964634B2

Reaction notes

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