Diethyl Ether → HCID 9884141, compound

HRID 1655282Notes

Reaction equation

HRID 1655282 reaction equation
[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:6]=[CH:5][C:4]([CH2:7][C@H:8]([NH:12][CH2:13][P:14]([O:18]C)([O:16]C)=[O:15])[C:9]([OH:11])=[O:10])=[CH:3][CH:2]=1.CCOCC>Br.C(O)(=O)C>[C:1]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:2]=[CH:3][C:4]([CH2:7][C@H:8]([NH:12][CH2:13][P:14]([OH:18])([OH:16])=[O:15])[C:9]([OH:11])=[O:10])=[CH:5][CH:6]=1

Participants

5

Reactant 2

HCID 3283Diethyl EtherHCID 10248130HCID 10248130, compound

Product 1

HCID 9884141HCID 9884141, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

(S)-3-(Biphenyl-4-yl)-2-(dimethylphosphonomethyl-amino)-propionic acid (278 mg, 0.76 mmol) is dissolved in a 30% solution of hydrobromic acid in acetic acid (10 mL) under nitrogen. After 2 hours, ether (50 mL) is added and the product precipitates. The mixture is kept at 0° for 18 hours and then filtered. The solid is dissolved in 0.1N sodium hydroxide (25 mL) and the insoluble material is filtered. The filtrate is acidified with 2N hydrochloric acid (5 mL). The gelatinous solid is filtered, washed with water and dried under high vacuum at 75° to give the (S)-3-(biphenyl-4-yl)-2-(phosphonomethyl-amino)-propionic acid as a white powder; m.p.: 241° (dec.); [α]D =+33.16 (c 0.95, 0.1N NaOH).

Workup

  1. customthe product precipitates
  2. waitThe mixture is kept at 0° for 18 hours
  3. filtrationfiltered
  4. dissolutionThe solid is dissolved in 0.1N sodium hydroxide (25 mL)
  5. filtrationthe insoluble material is filtered
  6. filtrationThe gelatinous solid is filtered
  7. washwashed with water
  8. customdried under high vacuum at 75°

Sources & evidence

ORD record
ord-eeb1c7467dca485187cd7423d0969a1c
Source dataset
uspto-grants-1993_10
Patent number
US05250522

Reaction notes

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