Hydrochloric Acid → L-Leucine

HRID 1600527Notes

Reaction equation

HRID 1600527 reaction equation
N1(C(C(C)(C)C[C@@H](C(N[C@@H](CCC2C=CC=CC=2)/C=C/S(C2C=CC=CC=2)(=O)=O)=O)N)=O)CCOCC1.Cl.NC(N)=O.N1CCOCC1.[NH2:49][C@H:50]([C:55]([OH:57])=[O:56])[CH2:51][CH:52]([CH3:54])[CH3:53].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:69]([O:76][C:77](=[O:84])[C@H:78]([CH2:80][CH:81]([CH3:83])[CH3:82])[NH2:79])[C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1>C(N(CC)CC)C>[NH2:49][C@H:50]([C:55]([OH:57])=[O:56])[CH2:51][CH:52]([CH3:54])[CH3:53].[NH2:79][C@H:78]([C:77]([O:76][CH2:69][C:70]1[CH:75]=[CH:74][CH:73]=[CH:72][CH:71]=1)=[O:84])[CH2:80][CH:81]([CH3:83])[CH3:82]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6451312L-Leucine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)HCID 70063332HCID 70063332, compoundHCID 70064382HCID 70064382, compound

Product 2

HCID 6106L-LeucineHCID 6451313Benzyl L-leucinate

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

Synthesis of (S)-(E)-3-(4-morpholine-carbonylleucyl)amino-5-phenyl-1-phenylsulfonyl-1-pentene, abbreviated Mu-Leu-HphVSPh, was as follows. Preparation of Mu-Leu-Hph was achieved by coupling of HCl.HphVSPh (described in the preparation of Mu-Phe-HphVSPh) with leucine morpholine urea (Mu-LeuOH). Mu-LeuOH was prepared in two steps, namely by treating the leucine benzyl ester p-toluenesulfonate (Bachem) with 4-morpholine chloride (Aldrich) in the presence of triethylamine (Aldrich) to give Mu-LeuOBzl in 99% yield. Hydrogenolysis over 5% palladium/charcoal in ethyl acetate afforded the desired product in quantitative yield.

Sources & evidence

ORD record
ord-46ecbd2cbafd493a9c1466c569e2be7b
Source dataset
uspto-grants-1999_11
Patent number
US05976858

Reaction notes

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