Sodium Hydroxide → HCID 14003420, compound

HRID 569751Notes

Reaction equation

HRID 569751 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:11][CH2:12][CH2:13][C:14]([O:16]CC)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH:10]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 14003419HCID 14003419, compound

Product 1

HCID 14003420HCID 14003420, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 370 ml of an ethanolic suspension containing 37.0 g of ethyl 6-(t-butoxycarbonylamino)-5-phenylhexanoate [prepared as described in step (b) above] were added 79 ml of water containing 8.8 g of sodium hydroxide. The reaction mixture was stirred for 1 hour at room temperature and then the solvent was distilled off under reduced pressure. The residue was mixed with ethyl acetate and water, and the aqueous layer was adjusted to a pH value of 3 by the addition of concentrated hydrochloric acid. The ethyl acetate layer was separated, washed with water and dried over anhydrous magnesium sulfate. Evaporation of the solvent gave quantitatively 6-(t-butoxycarbonylamino)-5-phenylhexanoic acid as a syrupy substance.

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionThe residue was mixed with ethyl acetate and water
  3. additionthe aqueous layer was adjusted to a pH value of 3 by the addition of concentrated hydrochloric acid
  4. customThe ethyl acetate layer was separated
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-08a04885cce543c280f4bed9721db295
Source dataset
uspto-grants-1988_03
Patent number
US04734410

Reaction notes

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