Tyrosine Methyl Ester → HCID 14502112, compound

HRID 984748Notes

Reaction equation

HRID 984748 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:14]([OH:16])=O)[CH2:10][CH:11]([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH3:39][O:40][C:41](=[O:52])[C@H:42]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([OH:51])=[CH:47][CH:46]=1)[NH2:43]>C(#N)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:10][CH:11]([CH3:12])[CH3:13])[C:14]([NH:43][C@@H:42]([CH2:44][C:45]1[CH:46]=[CH:47][C:48]([OH:51])=[CH:49][CH:50]=1)[C:41]([O:40][CH3:39])=[O:52])=[O:16])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 70652Tyrosine Methyl EsterHCID 757711-HydroxybenzotriazoleHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 14502112HCID 14502112, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-(tert-butoxycarbonyl)-L-leucine (7 g) in acetonitrile (100 ml), under a nitrogen atmosphere, was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.9 g) and 1-hydroxybenzotriazole (4.2 g). After stirring for 30 mins at 20° C. L-tyrosine methyl ester (5.5 g) was added and stirring was continued for 18 h. The mixture was concentrated in vacuo to ca. 10 ml and the residue was partitioned between 1M hydrochloric acid (200 ml) and ethyl acetate (100 ml). The layers were separated and the aqueous phase was further extracted with ethyl acetate (100 ml). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (100 ml), water (2×100 ml) and brine (50 ml), dried over sodium sulphate and evaporated in vacuo. The residue was co-evaporated with chloroform to give the title compound as a white foam (11.3 g, 98%). LCMS: Rt 3.11 min; m/z 409 (MH+).

Workup

  1. stirringstirring
  2. waitwas continued for 18 h
  3. concentrationThe mixture was concentrated in vacuo to ca. 10 ml
  4. customthe residue was partitioned between 1M hydrochloric acid (200 ml) and ethyl acetate (100 ml)
  5. customThe layers were separated
  6. extractionthe aqueous phase was further extracted with ethyl acetate (100 ml)
  7. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (100 ml), water (2×100 ml) and brine (50 ml)
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-d28506e4f1ac4dbd90c1424a3684f21a
Source dataset
uspto-grants-2005_03
Patent number
US06867192B1

Reaction notes

Loading…