Sodium Hydroxide → HCID 86647133, compound

HRID 2369799Notes

Reaction equation

HRID 2369799 reaction equation
[C:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:37])[CH2:23][N:24]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][C:26]([O:28]C)=[O:27])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1>[C:1]([O:5][C:6](=[O:38])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][NH:21][C:22](=[O:37])[CH2:23][N:24]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:25][C:26]([OH:28])=[O:27])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86647134HCID 86647134, compound

Product 1

HCID 86647133HCID 86647133, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15-[2-(tert-Butoxycarbonyl methoxycarbonylmethyl amino)acetylamino]pentadecanoic acid tert-butyl ester (0.22 g, 0.405 mmol) was dissolved in THF (5 mL) and 1 N NaOH (0.405 mL) was added. The mixture was stirred under nitrogen for 16 h. The mixture was concentrated under vacuum. The residue was suspended in AcOEt (ca 25 mL) and water (15 mL) and AcOH (3 mL) were added. The organic phase was isolated and washed with water (15 mL)+AcOH (1 mL), water (15 mL) and dried over magnesium sulphate, and concentrated under vacuum.

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. additionwater (15 mL) and AcOH (3 mL) were added
  3. customThe organic phase was isolated
  4. washwashed with water (15 mL)+AcOH (1 mL), water (15 mL)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-76703ffc487a4584a44f76c702e0e9eb
Source dataset
uspto-grants-2014_04
Patent number
US08710000B2

Reaction notes

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