Methanol → HCID 53996872, compound

HRID 266390Notes

Reaction equation

HRID 266390 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C@@H:12]([CH2:28][CH2:29][CH2:30][CH3:31])[C:13]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][C:23](OCC)=O)=[CH:18][CH:17]=2)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-:32].[Na+].[CH3:34][OH:35]>>[C:34]([CH2:23][CH2:22][C:19]1[CH:18]=[CH:17][C:16]([NH:15][C:13](=[O:14])[C@@H:12]([NH:11][S:8]([C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)(=[O:10])=[O:9])[CH2:28][CH2:29][CH2:30][CH3:31])=[CH:21][CH:20]=1)([OH:35])=[O:32]

Participants

4

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54545224HCID 54545224, compound

Product 1

HCID 53996872HCID 53996872, compound

Procedure

(S)-2-(4-chlorobenzenesulfonylamino)-N-(4-(ethoxycarbonylmethyl)phenyl)hexanamide (2.717 g) was dissolved in methanol (50 ml), 2N NaOH (8.72 ml) was added and the whole was stirred at room temperature overnight under argon. The reaction mixture was concentrated under reduced pressure to remove methanol. The concentrate was poured in 6N HCl while cooling with ice. The precipitated crystals were filtered and recrystallized from acetonitrile to obtain (S)-N-(4-(2-carboxyethyl)phenyl)-2-(4-chlorobenzenesulfonylamino)hexanamide (1.629 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto remove methanol
  3. additionThe concentrate was poured in 6N HCl
  4. temperaturewhile cooling with ice
  5. filtrationThe precipitated crystals were filtered
  6. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-52727f094ef94f3c8aa68565bc745a79
Source dataset
uspto-grants-1997_07
Patent number
US05650428

Reaction notes

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