Hydrochloric Acid → HCID 46206101, compound

HRID 2366483Notes

Reaction equation

HRID 2366483 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH:5]=[CH:6][C:7]=1[C:8]([O:10]C)=[O:9].O.[OH-].[Li+].Cl>O1CCCC1.O.CO>[C:20]([O:19][C:17]([N:13]1[CH2:14][CH2:15][CH2:16][C@@H:12]1[C:4]1[CH:5]=[CH:6][C:7]([C:8]([OH:10])=[O:9])=[C:2]([F:1])[CH:3]=1)=[O:18])([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 46205771HCID 46205771, compound

Product 1

HCID 46206101HCID 46206101, compoundYield 87.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 92A (2.65 g, 8.2 mmol) in tetrahydrofuran (20 mL) was added lithium hydroxide monohydrate (688 mg, 16.4 mmol) in 20 mL of water and methanol added until a transparent solution formed. This mixture was stirred at ambient temperature for 2 hours and acidified with 2N hydrochloric acid to pH 2. The mixture was concentrated to about 10 mL, diluted with water and let stand at ambient temperature overnight. The white solid was collected by filtration, washed with water and dried to give the title compound (2.21 g). Recrystallization from methanol and water gave 1.61 g of title compound.

Workup

  1. additionadded until a transparent solution
  2. customformed
  3. concentrationThe mixture was concentrated to about 10 mL
  4. additiondiluted with water
  5. waitlet stand at ambient temperature overnight
  6. filtrationThe white solid was collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-8b62a1a31f664ed3946de8a2e124c23b
Source dataset
uspto-grants-2014_04
Patent number
US08697736B2

Reaction notes

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