Hydrochloric Acid → HCID 59224906, compound

HRID 905643Notes

Reaction equation

HRID 905643 reaction equation
[BH4-].[Li+].[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([C:26](OC)=[O:27])=[CH:22][N:21]=1)=[O:19])=[O:9])([CH3:6])([CH3:5])[CH3:4].O.Cl>C1COCC1>[C:3]([O:7][C:8]([NH:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[NH:17][C:18]([C:20]1[CH:25]=[CH:24][C:23]([CH2:26][OH:27])=[CH:22][N:21]=1)=[O:19])=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 4148881Lithium borohydrideHCID 42626054HCID 42626054, compound

Product 1

HCID 59224906HCID 59224906, compoundYield 53%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice cooling, lithium tetrahydroborate (2.1 g, 100 mmol) was added to a solution of N-(2-t-butoxycarbonylaminophenyl)-5-methoxycarbonylpyridine-2-carboxylic acid amide (Reference Compound No. 2-1, 38 g, 100 mmol) in THF (400 mL), and then the reaction mixture was stirred for 3 hours. Under ice cooling, water (200 mL) and 1.0 M aqueous hydrochloric acid (300 mL) were added thereto, the whole was extracted with ethyl acetate (300 mL), and then the organic layer was washed with water (500 mL) and brine (400 mL). After the organic layer was dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. Ethyl acetate (20 mL) and hexane (30 mL) were added to the residue, and then the resulting solid was collected by filtration to give 18 g of the title reference compound as a white solid. (Yield 53%)

Workup

  1. extractionthe whole was extracted with ethyl acetate (300 mL)
  2. washthe organic layer was washed with water (500 mL) and brine (400 mL)
  3. dry with materialAfter the organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. additionEthyl acetate (20 mL) and hexane (30 mL) were added to the residue
  6. filtrationthe resulting solid was collected by filtration
  7. customto give 18 g of the title reference compound as a white solid

Sources & evidence

ORD record
ord-5635f6d8146f4971948d6ae0d7f16725
Source dataset
uspto-grants-2011_09
Patent number
US08012972B2

Reaction notes

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