Sodium Hydroxide → Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine

HRID 64643Notes

Reaction equation

HRID 64643 reaction equation
C[O:2][C:3](=[O:27])[C@H:4]([CH2:23][CH:24]([CH3:26])[CH3:25])[NH:5][CH2:6][CH2:7][C@H:8]([OH:22])[C@@H:9]([NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][CH:11]([CH3:13])[CH3:12].[OH-].[Na+]>O1CCOCC1.O>[C:18]([O:17][C:15]([NH:14][C@@H:9]([CH2:10][CH:11]([CH3:13])[CH3:12])[C@@H:8]([OH:22])[CH2:7][CH2:6][NH:5][C@H:4]([C:3]([OH:27])=[O:2])[CH2:23][CH:24]([CH3:25])[CH3:26])=[O:16])([CH3:21])([CH3:19])[CH3:20]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 13672671Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucine methyl ester

Product 1

HCID 13672673Nalpha-[4(S)-tert-Butoxycarbonylamino-3(S)-hydroxy-6-methylheptyl]-L-leucineYield 83%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

2 (700 mg) was dissolved in dioxane (8 ml), diluted with H2O (8 ml) and treated with four portions (2 ml each) of 1N NaOH (aqueous) over a 1.5 hour period. The aqueous dioxane was removed in vacuo and the white solid residue dissolved in H2O (10 ml). The product was precipitated by acidification with 1N HCl and collected by filtration to give 3 as a fine white powder (560 mg, 83% yield) after drying.

Workup

  1. customThe aqueous dioxane was removed in vacuo
  2. dissolutionthe white solid residue dissolved in H2O (10 ml)
  3. customThe product was precipitated by acidification with 1N HCl
  4. filtrationcollected by filtration

Sources & evidence

ORD record
ord-0360072153b74d609518361aad83fa96
Source dataset
uspto-grants-1986_09
Patent number
US04609641

Reaction notes

Loading…