Hydrochloric Acid → HCID 59201245, compound

HRID 1942300Notes

Reaction equation

HRID 1942300 reaction equation
[Li+].[OH-].[F:3][CH:4]([F:34])[O:5][CH2:6][C@H:7]([N:13]1[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]([O:22]C)=[O:21])[CH2:15][C@H:14]1[C:24]1[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11].Cl.C([O-])(O)=O.[Na+]>O.C1COCC1>[F:34][CH:4]([F:3])[O:5][CH2:6][C@H:7]([N:13]1[CH2:18][CH2:17][C@@H:16]([CH2:19][C:20]([OH:22])=[O:21])[CH2:15][C@H:14]1[C:24]1[CH:25]=[CH:26][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:28][CH:29]=1)[CH2:8][CH2:9][CH:10]([CH3:12])[CH3:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 516892Sodium BicarbonateHCID 59201237HCID 59201237, compound

Product 1

HCID 59201245HCID 59201245, compoundYield 94.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of LiOH (5 mg, 0.209 mmol) in H2O (0.5 ml) was added to a stirred solution of the ester (Step 1, 13 mg, 0.028 mmol) in THF (1 ml) at RT. The mixture was stirred at RT for 3 days. 2N HCl (0.5 ml) was added. The pH of the aqueous layer was adjusted to ˜7 with NaHCO3 (aq). The aqueous layer was extracted with DCM (×3). The combined extracts were dried (Na2SO4), filtered and evaporated to give the title compound (12 mg) as a colourless solid after evaporation from pentane. M/Z 452 (MH+).

Workup

  1. extractionThe aqueous layer was extracted with DCM (×3)
  2. dry with materialThe combined extracts were dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-e0bc7c6894dd42ad9308fb4ef6cfca33
Source dataset
uspto-grants-2013_03
Patent number
US08389547B2

Reaction notes

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