Hydrochloric Acid → HCID 22052433, compound

HRID 1831828Notes

Reaction equation

HRID 1831828 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH2:10][N:11]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:12][C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=2[Cl:20])[CH:5]=1.O.[OH-].[Na+].Cl>O1CCOCC1>[C:24]([O:23][C:21]([N:11]([CH2:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[C:3]([OH:28])=[O:2])[CH2:12][C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=[O:22])([CH3:27])([CH3:25])[CH3:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 69652293HCID 69652293, compound

Product 1

HCID 22052433HCID 22052433, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

0.85 g (2.00 mmol) of 3{[tert-Butoxycarbonyl-(2,4-dichloro-benzyl)-amino]-methyl}-benzoic acid methyl ester was dissolved in 20 ml of dioxan. 5 ml of water and 2N aqueous NaOH was added to the solution to give a pH of 13. The reaction solution was stirred for 5 h then poured into water. The resulting solution was cooled to 0° C. and concentrated hydrochloric acid was added to give a pH of 3. The product was extracted 3 times with ethyl acetate. The organic phase was dried over magnesium sulphate, filtered and the solvent was removed under reduced pressure.

Workup

  1. customto give a pH of 13
  2. customto give a pH of 3
  3. extractionThe product was extracted 3 times with ethyl acetate
  4. dry with materialThe organic phase was dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-034896cfa6e04257847a3cc3c76f6bc1
Source dataset
uspto-grants-2006_06
Patent number
US07067665B2

Reaction notes

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