Sodium Hydroxide → HCID 86746179, compound

HRID 465623Notes

Reaction equation

HRID 465623 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@@H:16]([CH2:23][CH2:24][CH2:25][C:26]2[CH:27]=[N:28][CH:29]=CC=2)CCC(OC)=O)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-:32].[Na+].[O:34]1[CH2:39]COCC1>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]([CH2:13][CH:14]([CH2:15][CH2:16][CH2:23][C:24]2[CH:29]=[N:28][CH:27]=[CH:26][CH:25]=2)[CH2:7][CH2:2][CH2:3][CH3:4])[C:39]([OH:34])=[O:32])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 10412273HCID 10412273, compound

Product 1

HCID 86746179HCID 86746179, compound

Procedure

A mixture of methyl (R)-8(p-chlorophenylsulfonamido)-4-[3-(3-pyridyl)propyl]octanoate (1.5 g, 3.2 mmol), dioxane (15 ml) and 1N sodium hydroxide (6.6 ml, 6.6 mmol) is stirred at room temperature for 62 hours. The solvent is evaporated and the residue taken up in water and the mixture is adjusted to pH=5.0. The product separates an an oil which solidifies rapidly. It is filtered off and washed with water (4×5 ml) and ether (4×5 ml). Upon drying under vacuum at 60° C. for 18 hours, (R)-8-(p-chlorophenylsulfonamido-4-[3-(3-pyridyl)propyl]octanoic acid is obtained as a white solid, m.p. 113°-114° C.

Workup

  1. customThe solvent is evaporated
  2. filtrationIt is filtered off
  3. washwashed with water (4×5 ml) and ether (4×5 ml)
  4. customUpon drying under vacuum at 60° C. for 18 hours

Sources & evidence

ORD record
ord-7f3ec74374254aecaee623a1b2f0b990
Source dataset
uspto-grants-1992_10
Patent number
US05153214

Reaction notes

Loading…