Hydrochloric Acid → N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl ester

HRID 434409

Reaction equation

HRID 434409 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:13]([O:15][P:16]([CH2:28][C:29]([OH:31])=O)([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:17])[CH3:14].Cl.[CH3:33][O:34][C:35](=[O:46])[C@H:36]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([OH:45])=[CH:41][CH:40]=1)[NH2:37]>C(#N)C.CO.C(N(CC)CC)C>[CH2:13]([O:15][P:16]([CH2:28][C:29]([NH:37][C@H:36]([C:35]([O:34][CH3:33])=[O:46])[CH2:38][C:39]1[CH:40]=[CH:41][C:42]([OH:45])=[CH:43][CH:44]=1)=[O:31])([CH2:18][CH2:19][CH2:20][CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)=[O:17])[CH3:14]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 70652Tyrosine Methyl EsterHCID 13136848[Ethoxy(4-phenylbutyl)phosphoryl]acetic acid

Product 1

HCID 131713050N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl esterYield 88%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6342AcetonitrileSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
0 °C

Procedure

1,1'-Carbonyldiimidazole (0.56 g) was added portionwise to a cooled (0° C.) solution of [ethoxy(4-phenylbutyl)phosphinyl]acetic acid (0.98 g) in 70 ml of acetonitrile. This reaction mixture was stirred under argon at 0° C. for 1.5 hours. The HCl salt of L-tyrosine methyl ester (0.8 g) was dissolved in methanol and neutralized with triethylamine (0.35 g). This solution was concentrated in vacuo, dissolved in 10 ml of warm acetonitrile and added dropwise to the above solution of activated phosphinic acid ester sidechain. The reaction was stirred overnight under argon and then concentrated in vacuo. A solution of the pot residue in dichloromethane was washed (H2O, aqueous NaHCO3, brine), dried (MgSO4) and filtered to yield 1.4 g of N-[[ethoxy(4-phenylbutyl)phosphinyl]acetyl]-L-tyrosine, methyl ester.

Workup

  1. concentrationThis solution was concentrated in vacuo
  2. dissolutiondissolved in 10 ml of warm acetonitrile
  3. additionadded dropwise to the above solution of activated phosphinic acid ester sidechain
  4. stirringThe reaction was stirred overnight under argon
  5. concentrationconcentrated in vacuo
  6. washA solution of the pot residue in dichloromethane was washed (H2O, aqueous NaHCO3, brine)
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered

Sources & evidence

ORD record
ord-37fd470cc21344d8ba7464aa0b158bd6
Source dataset
uspto-grants-1983_08
Patent number
US04396772

Linked notes

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