Hydrochloric Acid → HCID 56943060, compound

HRID 467994Notes

Reaction equation

HRID 467994 reaction equation
C[O:2][C:3]([C:5]1([CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]2([C:23](=[O:28])[NH:24][CH:25]3[CH2:27][CH2:26]3)[CH2:22][CH2:21]2)[CH2:7][CH2:6]1)=[O:4].[OH-].[K+].Cl>CO.O>[CH:25]1([NH:24][C:23]([C:20]2([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:5]3([C:3]([OH:4])=[O:2])[CH2:7][CH2:6]3)[CH2:22][CH2:21]2)=[O:28])[CH2:27][CH2:26]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 56943059HCID 56943059, compound

Product 1

HCID 56943060HCID 56943060, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

To a solution of product of Example 34 (0.7 g, 1.9 mmol) in methanol (7 mL) was added KOH (0.36 g, 6.4 mmol) in water (2.1 mL) and the reaction mixture was stirred at 60° C. over a period of 16 h. The crude product obtained upon evaporation of the solvent was diluted with water (5.0 mL), acidified to pH=2 (1.5N HCl), extracted with ethyl acetate (100 mL×2). The organic layer was dried over sodium sulphate and concentrated. The residue obtained upon evaporation of the volatiles was purified by silica gel (230-400) column (50% ethyl acetate in petroleum ether) to give product as white solid 0.51 g (76%). mp: 95.3° C.-97.7° C.

Workup

  1. customThe crude product obtained upon evaporation of the solvent
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. dry with materialThe organic layer was dried over sodium sulphate
  4. concentrationconcentrated
  5. customThe residue obtained upon evaporation of the volatiles
  6. customwas purified by silica gel (230-400) column (50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-71a7752f46bb45d8af2b6c1460e31aef
Source dataset
uspto-grants-2014_01
Patent number
US08623897B2

Reaction notes

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