Hydrochloric Acid → HCID 10248130, compound

HRID 1655284Notes

Reaction equation

HRID 1655284 reaction equation
C[O:2][C:3](=[O:26])[C@@H:4]([NH:18][CH2:19][P:20]([O:24][CH3:25])([O:22][CH3:23])=[O:21])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[CH:8][CH:7]=1.[OH-].[Na+].Cl>CO>[C:9]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:7][C:6]([CH2:5][C@H:4]([NH:18][CH2:19][P:20]([O:24][CH3:25])([O:22][CH3:23])=[O:21])[C:3]([OH:26])=[O:2])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 54416045HCID 54416045, compound

Product 1

HCID 10248130HCID 10248130, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

(S)-3-(Biphenyl-4-yl)-2-[(dimethylphosphonomethyl)-amino]-propionic acid methyl ester (5 g, 13.2 mmol) is dissolved in methanol (60 mL) and cooled to 0°. 1N Sodium hydroxide (19.8 mL, 19.8 mmol) is added dropwise. The solution is stirred at room temperature for 4 hours, then neutralized with 1N hydrochloric acid (20.2 mL, 20.2 mmol). The solvent is removed in vacuo at 10° from the gelatinous solution. The residue is extracted with methylene chloride (3×20 mL). The combined organic layers are washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated in vacuo. The crude solid is triturated with acetonitrile, filtered and washed with ether. (S)-3-(Biphenyl-4-yl)-2-[(dimethylphosphonomethyl)-amino]-propionic acid is obtained as a white solid that is dried under vacuum at 60° for 16 hours, [α]D =+77.34 (c 0.83, MeOH).

Workup

  1. temperaturecooled to 0°
  2. customThe solvent is removed in vacuo at 10° from the gelatinous solution
  3. extractionThe residue is extracted with methylene chloride (3×20 mL)
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude solid is triturated with acetonitrile
  9. filtrationfiltered
  10. washwashed with ether

Sources & evidence

ORD record
ord-52760878e63c4bcd8a85a26cf69bcb3f
Source dataset
uspto-grants-1993_10
Patent number
US05250522

Reaction notes

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