Sodium borohydride → 2-{2-[(tert-Butoxycarbonyl)amino]ethoxy}-5-chloro-3-(1-hydroxyethyl)-6-methylbenzoic acid

HRID 626823Notes

Reaction equation

HRID 626823 reaction equation
[BH4-].[Na+].[C:3]([C:6]1[C:7]([O:17][CH2:18][CH2:19][NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])=[C:8]([C:12]([CH3:16])=[C:13]([Cl:15])[CH:14]=1)[C:9]([OH:11])=[O:10])(=[O:5])[CH3:4]>CO>[C:24]([O:23][C:21]([NH:20][CH2:19][CH2:18][O:17][C:7]1[C:6]([CH:3]([OH:5])[CH3:4])=[CH:14][C:13]([Cl:15])=[C:12]([CH3:16])[C:8]=1[C:9]([OH:11])=[O:10])=[O:22])([CH3:25])([CH3:27])[CH3:26]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 866975173-Acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acid

Product 1

HCID 866975182-{2-[(tert-Butoxycarbonyl)amino]ethoxy}-5-chloro-3-(1-hydroxyethyl)-6-methylbenzoic acidYield 80.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium tetrahydroborate (6.1 mg, 0.16 mmol) was added to a mixture of 3-acetyl-2-{2-[(tert-butoxycarbonyl)amino]ethoxy}-5-chloro-6-methylbenzoic acid (40 mg, 0.1 mmol) in methanol (0.50 mL) at 0° C. and the reaction was stirred at room temperature for 1 hour. The solvent was removed and the residue was diluted with ethyl acetate, washed with saturated sodium bicarbonate, adjusted the pH to 5 with 1 N hydrogen chloride solution, washed with brine, dried over sodium sulfate, filtered and concentrated to give the desired compound (30 mg, 70%). LCMS calculated for C17H24ClNO6Na (M+Na)+: m/z=396.1; found: 396.0.

Workup

  1. customThe solvent was removed
  2. additionthe residue was diluted with ethyl acetate
  3. washwashed with saturated sodium bicarbonate
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-e4c65447b7b04ed284bfe0d2a824a45a
Source dataset
uspto-grants-2016_04
Patent number
US09309251B2

Reaction notes

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