Hydrogen Bromide → HCID 54206137, compound

HRID 328090Notes

Reaction equation

HRID 328090 reaction equation
C(N)C1C=CC=CC=1.C(OC([N:19]1[CH2:32][CH2:31][CH2:30][C@H:20]1[C:21]([NH:23][C@H:24]([P:26](=[O:29])([OH:28])[OH:27])[CH3:25])=[O:22])=O)C1C=CC=CC=1.Br.C1OC1C>C(O)(=O)C.CO>[NH:19]1[CH2:32][CH2:31][CH2:30][C@H:20]1[C:21]([NH:23][C@H:24]([P:26](=[O:27])([OH:28])[OH:29])[CH3:25])=[O:22]

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 6378Propylene OxideHCID 7504BenzylamineHCID 22796733HCID 22796733, compound

Product 1

HCID 54206137HCID 54206137, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 887MethanolSolvent2×

Procedure

2.3 of the benzylamine salt of (1R)-1-[(N-benzyloxycarbonyl-L-prolyl)amino] -ethylphosphonic acid were added to a stirred solution (45%) of hydrogen bromide in glacial acetic acid and washed in with 2.5 ml of glacial acetic acid. The mixture was stirred at room temperature for 6 hours and then 75ml of ether were added while stirring. The supernatant was decanted and the residue was again treated with 75ml of ether. The granular solid obtained was dissolved in 30ml of methanol and the solution treated with a solution of 5ml of propylene oxide in 10ml of methanol. After standing for several hours, the precipitate was filtered off, washed with methanol and ether and dried. Crystallization from water/ethanol gave 0.39 g of (1R)-1-(L-prolylamino)-ethylphosphonic acid of melting point 291°-293° C (decomposition); [α]D20 = - 92.3°(c = 0.5% in water).

Workup

  1. washwashed in with 2.5 ml of glacial acetic acid
  2. addition75ml of ether were added
  3. stirringwhile stirring
  4. customThe supernatant was decanted
  5. additionthe residue was again treated with 75ml of ether
  6. customThe granular solid obtained
  7. waitAfter standing for several hours
  8. filtrationthe precipitate was filtered off
  9. washwashed with methanol and ether
  10. customdried
  11. customCrystallization from water/ethanol

Sources & evidence

ORD record
ord-5772042e17564a62b240ee0268f5bdff
Source dataset
uspto-grants-1977_04
Patent number
US04016148

Reaction notes

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