Benzenamine hydrochloride (1:1) → HCID 70558031, compound

HRID 1413410Notes

Reaction equation

HRID 1413410 reaction equation
C1C=CC(N)=CC=1.Cl.C(O[C:17]([N:19]([CH2:21][C:22]([NH:24][C@H:25]([C:34]([NH:36][C@H:37]([C:39]([NH:41][C@H:42]([P:44](=[O:47])([OH:46])[OH:45])[CH3:43])=[O:40])[CH3:38])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)=[O:23])C)=O)C1C=CC=CC=1.[H][H]>C(O)(=O)C.[Pd]>[NH:19]([CH2:21][C:22]([NH:24][C@H:25]([C:34]([NH:36][C@H:37]([C:39]([NH:41][C@H:42]([P:44](=[O:45])([OH:47])[OH:46])[CH3:43])=[O:40])[CH3:38])=[O:35])[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1)=[O:23])[CH3:17]

Participants

6

Reactant 3

HCID 8870Benzenamine hydrochloride (1:1)HCID 53855109HCID 53855109, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70558031HCID 70558031, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent2×

Procedure

The aniline salt of (1R)-1-[(N-benzyloxycarbonyl-sarcosyl-L-tyrosyl-L-alanyl)amino]-ethylphosphonic acid was suspended in acetic acid and 10% palladium-on-carbon was added under argon. Acetic acid was then added. The mixture was stirred overnight at room temperature and then hydrogenated until the uptake of hydrogen ceased. The catalyst was filtered off and the filtrate was evaporated. The residual solid was triturated with methanol, filtered off, washed and dried. The solid was purified by reprecipitation from aqueous hydrochloric acid/ethanol with propylene oxide to give (1R)-1-(N-sarcosyl-L-tyrosyl-L-alanylamino)-ethylphosphonic acid of melting point 275°-277° C. (decomposition).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated
  3. customThe residual solid was triturated with methanol
  4. filtrationfiltered off
  5. washwashed
  6. customdried
  7. customThe solid was purified by reprecipitation from aqueous hydrochloric acid/ethanol with propylene oxide

Sources & evidence

ORD record
ord-deac356e86a848db9e8dc5f716d57809
Source dataset
uspto-grants-1981_02
Patent number
US04250085

Reaction notes

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