Hydrochloric Acid → HCID 21963949, compound

HRID 2212376Notes

Reaction equation

HRID 2212376 reaction equation
[OH-].[Li+].C([O:5][C:6](=[O:38])[CH:7]([S:34]([CH3:37])(=[O:36])=[O:35])[CH2:8][CH2:9][CH:10]1[CH2:15][CH2:14][C:13]([S:24]([C:27]2[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=2)(=[O:26])=[O:25])([C:16]2[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=2[F:23])[CH2:12][CH2:11]1)C.Cl>O.O1CCCC1>[Cl:33][C:30]1[CH:31]=[CH:32][C:27]([S:24]([C:13]2([C:16]3[CH:21]=[C:20]([F:22])[CH:19]=[CH:18][C:17]=3[F:23])[CH2:12][CH2:11][CH:10]([CH2:9][CH2:8][CH:7]([S:34]([CH3:37])(=[O:35])=[O:36])[C:6]([OH:38])=[O:5])[CH2:15][CH2:14]2)(=[O:25])=[O:26])=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 21048985HCID 21048985, compound

Product 1

HCID 21963949HCID 21963949, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide (21 mg, 0.88 mmol) in water (700 mL) was added to the product from Example 108 (100 mg, 0.18 mmol) in tetrahydrofuran (2 mL). The resulting mixture was stirred vigorously for 12 hours, then poured into 1M aqueous hydrochloric acid (20 mL) and extracted with ethyl acetate (2×40 mL). The combined organic layers were dried (NaSO4), and concentrated. The residue was purified using column chromatography on silica, eluting with 95/5/0.5 dichloromethane/methanol/acetic acid to give the title compound (79 mg).

Workup

  1. extractionextracted with ethyl acetate (2×40 mL)
  2. dry with materialThe combined organic layers were dried (NaSO4)
  3. concentrationconcentrated
  4. customThe residue was purified
  5. washeluting with 95/5/0.5 dichloromethane/methanol/acetic acid

Sources & evidence

ORD record
ord-beb86aee187b49d282c66072cb2a9dbd
Source dataset
uspto-grants-2006_09
Patent number
US07101895B2

Reaction notes

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