Leucine, N-carboxy-, N-benzyl ester, L- → HCID 57163670, compound

HRID 984749Notes

Reaction equation

HRID 984749 reaction equation
[C:1]([NH:11][C@H:12]([C:17]([OH:19])=O)[CH2:13][CH:14]([CH3:16])[CH3:15])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].Cl.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[C:42]([O:46][C:47](=[O:58])[C@H:48]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([OH:57])=[CH:53][CH:52]=1)[NH2:49])([CH3:45])([CH3:44])[CH3:43]>C(#N)C>[CH2:4]([O:3][C:1]([NH:11][C@@H:12]([CH2:13][CH:14]([CH3:15])[CH3:16])[C:17]([NH:49][C@@H:48]([CH2:50][C:51]1[CH:56]=[CH:55][C:54]([OH:57])=[CH:53][CH:52]=1)[C:47]([O:46][C:42]([CH3:44])([CH3:43])[CH3:45])=[O:58])=[O:19])=[O:2])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 74840Leucine, N-carboxy-, N-benzyl ester, L-HCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6950582L-Tyrosine 1,1-dimethylethyl ester

Product 1

HCID 57163670HCID 57163670, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of N-carbobenzyloxy-L-leucine (8.6 g) in acetonitrile (150 ml), under a nitrogen atmosphere, was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (6.83 g) and 1-hydroxybenzotriazole (4.81 g). After stirring for 30 mins at 20° C. L-tyrosine tert-butyl ester (7.7 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 (300 ml) and ethyl acetate (150 ml). The layers were separated and the aqueous phase was further extracted with ethyl acetate (150 ml). The combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (150 ml), water (2×150 ml) and brine (100 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 (15 g, 96%). LCMS: Rt 3.56 min; m/z 485 (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 (300 ml) and ethyl acetate (150 ml)
  5. customThe layers were separated
  6. extractionthe aqueous phase was further extracted with ethyl acetate (150 ml)
  7. washThe combined organic extracts were washed with saturated aqueous sodium hydrogen carbonate (150 ml), water (2×150 ml) and brine (100 ml)
  8. dry with materialdried over sodium sulphate
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-3f59995ff68d40fca1b31a5b73d632d9
Source dataset
uspto-grants-2005_03
Patent number
US06867192B1

Reaction notes

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