Hydrochloric Acid → HCID 22930486, compound

HRID 2247420Notes

Reaction equation

HRID 2247420 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:18]2[CH:19]=[C:20]([CH:25]=[CH:26][CH:27]=2)[C:21](OC)=[O:22])[CH:13]=[CH:14][C:15]=1[O:16][CH3:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Li+].Cl>O1CCCC1>[OH:22][CH2:21][C:20]1[CH:19]=[C:18]([C:12]2[CH:13]=[CH:14][C:15]([O:16][CH3:17])=[C:10]([CH:11]=2)[CH2:9][NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 59219273HCID 59219273, compound

Product 1

HCID 22930486HCID 22930486, compoundYield 81.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 3-(3-{[(t-butoxycarbonyl)amino]-methyl}-4-methoxyphenyl)benzoate (1.943 g) was dissolved in 30 ml of tetrahydrofuran, 250 mg of lithium borohydride was added thereto, and the mixture was stirred at room temperature for 2 weeks. 1N Hydrochloric acid was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by silica gel column, to give 1.47 g of the title compound in the 3:1→1:1 hexane-ethyl acetate fraction.

Workup

  1. extractionwas then extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed
  4. customThe residue was purified by silica gel column

Sources & evidence

ORD record
ord-4ef40484a0c0466991c6409fdd8bce5e
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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