Hydrochloric Acid → HCID 67253234, compound

HRID 389908Notes

Reaction equation

HRID 389908 reaction equation
[OH:1][CH2:2][C@@:3]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:5]([OH:7])=O)[NH2:4].[Cl:14][C:15]1[CH:16]=[C:17]([N:22]=[C:23]=[O:24])[CH:18]=[CH:19][C:20]=1[Cl:21].Cl>[OH-].[Na+].O1CCOCC1>[Cl:14][C:15]1[CH:16]=[C:17]([N:22]2[C:5](=[O:7])[C@@:3]([CH2:2][OH:1])([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[NH:4][C:23]2=[O:24])[CH:18]=[CH:19][C:20]=1[Cl:21]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 76073,4-Dichlorophenyl isocyanate2×HCID 12175874HCID 12175874, compound

Product 1

HCID 67253234HCID 67253234, compound

Reagents, catalysts & solvents 2

HCID 14798Sodium HydroxideSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

217 mg of (S)-2-hydroxymethyl-2-phenylglycine (prepared according to A. Olma, Polish J. Chem., 70, (1996), 1442-1447) are dissolved in 5 mL of 0.5 N aqueous sodium hydroxide. 300 mg of 3,4-dichlorophenyl isocyanate dissolved in 5 mL dioxan are slowly added over 10 min then the mixture is stirred for 1 h, the pH is around 7 to 7.5. 3 mL of 0.5 N aqueous sodium hydroxide are added to make the pH alkaline then 300 mg of 3,4-dichlorophenyl isocyanate dissolved in 5 mL dioxan are slowly added again. The mixture is stirred for 1 further hour at room temperature then 12N hydrochloric acid is added to acidic pH and the mixture is heated for 1 h at reflux temperature. The dioxan is removed by evaporation under vacuum, the aqueous phase is extracted with ethyl acetate. The extracts are washed with brine, dried over magnesium sulfate and evaporated to dryness. The residue is purified over silica gel while eluting with a gradient mixture from heptane to pure ethyl acetate to provide expected product.

Workup

  1. additionare slowly added over 10 min
  2. additionare slowly added again
  3. stirringThe mixture is stirred for 1 further hour at room temperature
  4. temperaturethe mixture is heated for 1 h
  5. temperatureat reflux temperature
  6. customThe dioxan is removed by evaporation under vacuum
  7. extractionthe aqueous phase is extracted with ethyl acetate
  8. washThe extracts are washed with brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated to dryness
  11. customThe residue is purified over silica gel
  12. washwhile eluting with a gradient mixture from heptane to pure ethyl acetate

Sources & evidence

ORD record
ord-72dcb8055d3b46f4921e729d5b522562
Source dataset
uspto-grants-2013_02
Patent number
US08383608B2

Reaction notes

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