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Hydrochloric Acid → (S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[2-(1,1-dimethylethoxy)-2-oxoethyl]-benzenepropanoic acid

HRID 487799
Notes
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Reaction equation

HRID 487799 reaction equation
C[O:2][C:3](=[O:28])[C@@H:4]([NH:20][C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:7]=1.Cl>CO.[OH-].[Na+].CCOCC>[CH3:26][C:24]([CH3:27])([O:23][C:21]([NH:20][C@@H:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[CH:8][CH:7]=1)[C:3]([OH:28])=[O:2])=[O:22])[CH3:25]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 14560606HCID 14560606, compound

Product 1

HCID 14560610(S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[2-(1,1-dimethylethoxy)-2-oxoethyl]-benzenepropanoic acidYield 77.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent
HCID 14798
Sodium Hydroxide
Solvent

Procedure

A solution of 1.471 g of (S)-alpha-[[(1,1-dimethylethoxy)carbonyl]amino]-4-[2-(1,1-dimethylethoxy) -2-oxoethyl]benzenepropanoic acid methyl ester in 25 mL of methanol and 5 mL of 1N sodium hydroxide solution was stirred at room temperature for 2 hours. The mixture was acidified with a slight excess of hydrochloric acid, was diluted with 100 mL of ether, and was washed with water and saturated sodium chloride solution. The residue obtained after filtration and evaporation was chromatographed over 100 g of silica gel, eluting with 40:59:0.5 ethyl acetate-hexane-acetic acid. The product containing fractions were combined evaporated, diluted with toluene and evaporated finally under high vacuum to give 1.105 g of (S)-alpha-[[(1,1-dimethylethoxy) carbonyl]amino]-4-[2-(1,1-dimethylethoxy)-2-oxoethyl]benzene-propanoic acid [a]D +21.41 (ethanol).

Workup

  1. washwas washed with water and saturated sodium chloride solution
  2. customThe residue obtained
  3. filtrationafter filtration and evaporation
  4. customwas chromatographed over 100 g of silica gel
  5. washeluting with 40:59:0.5 ethyl acetate-hexane-acetic acid
  6. additionThe product containing fractions
  7. customwere combined evaporated
  8. additiondiluted with toluene
  9. customevaporated finally under high vacuum

Sources & evidence

ORD record
ord-4a1500bc9d1940c3b71b669d2fc4bd1e
Source dataset
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05296608

Reaction notes

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