Hydrochloric Acid → HCID 10393275, compound

HRID 487233Notes

Reaction equation

HRID 487233 reaction equation
[C:1]1([O:7][P:8]([CH2:17][NH:18][C@@H:19]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:38][CH:37]=2)[C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)=[O:26])=[O:21])([O:10]C2C=CC=CC=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl>C1COCC1>[C:1]1([O:7][P:8]([CH2:17][NH:18][C@@H:19]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[CH:40][CH:41]=2)[C:20]([NH:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)=[O:26])=[O:21])([OH:10])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 10258691HCID 10258691, compound

Product 1

HCID 10393275HCID 10393275, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Benzyl (S)-N-[2-(diphenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate (720 mg, 1.1 mmol) is dissolved in THF (15 mL) and treated with 2N hydrochloric acid. The solution is stirred at room temperature for 8 hours. The precipitate is filtered. It can be further purified by column chromatography on silica gel, eluting with a mixture of methylene chloride-methanol-acetic acid (95/5/25), to obtain benzyl (S)-N-[2-(monophenylphosphonomethylamino)-3-(4-biphenylyl)-propionyl]-3-aminopropionate m.p. 243°-244°.

Workup

  1. filtrationThe precipitate is filtered
  2. customIt can be further purified by column chromatography on silica gel
  3. washeluting with a mixture of methylene chloride-methanol-acetic acid (95/5/25)

Sources & evidence

ORD record
ord-4b2988b4aa094aca8f4f87058e0c56e8
Source dataset
uspto-grants-1994_03
Patent number
US05294632

Reaction notes

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