Sodium Hydroxide → (S)-3-[(5-tert-butoxycarbonylamino-pyridin-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid

HRID 1428219Notes

Reaction equation

HRID 1428219 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([NH:17][C@@:18]2([C:23]([O:25]CCCC)=[O:24])[CH2:22][CH2:21][O:20][CH2:19]2)=[O:16])[CH:12]=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1[CH:10]=[C:11]([C:15]([NH:17][C@@:18]2([C:23]([OH:25])=[O:24])[CH2:22][CH2:21][O:20][CH2:19]2)=[O:16])[CH:12]=[N:13][CH:14]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68026189n-butyl(S)-3-[(5-tert-butoxycarbonylamino-pyridin-3-carbonyl)-amino]-tetra-hydrofuran-3-carboxylate

Product 1

HCID 68026203(S)-3-[(5-tert-butoxycarbonylamino-pyridin-3-carbonyl)-amino]-tetrahydrofuran-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of n-butyl(S)-3-[(5-tert-butoxycarbonylamino-pyridin-3-carbonyl)-amino]-tetra-hydrofuran-3-carboxylate (29.7 mmol) in 150 mL methanol was combined with 60 mL of 1N sodium hydroxide solution and stirred for three hours at ambient temperature. Then the methanol was distilled off, the solution was then washed with 50 mL tert-butylmethylether and then adjusted to pH 3 with 4N hydrochloric acid. The product that then precipitated was filtered off and further reacted without purification.

Workup

  1. distillationThen the methanol was distilled off
  2. washthe solution was then washed with 50 mL tert-butylmethylether
  3. customThe product that then precipitated
  4. filtrationwas filtered off
  5. customfurther reacted without purification

Sources & evidence

ORD record
ord-37f57ab683444faf83226f4ff6900cbb
Source dataset
uspto-grants-2015_01
Patent number
US08937073B2

Reaction notes

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