Sodium Hydroxide → HCID 86658639, compound

HRID 1625692Notes

Reaction equation

HRID 1625692 reaction equation
[C:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C@H:15]([NH:20]C(=O)C(F)(F)F)[C:16]([O:18]C)=[O:17])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[OH-].[Na+].[ClH:31].COC(=O)[C@@H](NC(=O)C(F)(F)F)CCCCN>CO>[Cl-:31].[C:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([NH:10][CH2:11][CH2:12][CH2:13][CH2:14][C@@H:15]([C:16]([OH:18])=[O:17])[NH3+:20])=[O:9])=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 86658640HCID 86658640, compoundHCID 86658641HCID 86658641, compound

Product 1

HCID 86658639HCID 86658639, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

(S)-methyl 6-(4-acetylbenzamido)-2-(2,2,2-trifluoroacetamido)hexanoate (TU2982-136) (0.473 g) was treated 1 N aq NaOH (2.36 mL) in 10 mL MeOH at ambient temperature for 18 hours. LC-MS analysis was used to reveal the complete hydrolysis of the methyl ester, while maintaining the trifluoroamide moiety intact. The reaction was heated at 60° C. for 5 hours, at which time the amide hydrolysis was almost complete, as indicated by LC-MS analysis. The reaction mixture was cooled and concentrated under reduced pressure. The residue was treated with excess 1 N aq HCl, and concentrated to dryness under reduced pressure, affording ((S)-5-(4-acetylbenzamido)-1-carboxypentan-1-aminium chloride (TU3000-004) as a slightly yellow solid. MS (ESI+): calcd. 293.14. found 293.20 (MH+).

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was treated with excess 1 N aq HCl
  4. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-42e04e340a3a43eeb0e256ad0fc64a92
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

Loading…