Dicyclohexylcarbodiimide → Benzyl L-leucinate

HRID 1410326Notes

Reaction equation

HRID 1410326 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:18]([OH:20])=[O:19])[CH2:3][C:4]1[CH:9]=CC(OCC2C=CC=CC=2)=C[CH:5]=1.[CH:28]1[CH:29]=[CH:30][C:31]2N(O)N=N[C:32]=2[CH:33]=1.[CH2:38]1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C.CN(C=O)C>[NH2:1][C@H:2]([C:18]([O:20][CH2:38][C:32]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:33]=1)=[O:19])[CH2:3][CH:4]([CH3:5])[CH3:9]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 98763O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine

Product 1

HCID 6451313Benzyl L-leucinate

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

p-tosylate (22.2 kg; Bachem AG, Switzerland) was suspended in ethyl acetate (108 L), then TEA (about 7.1 L) was added at room temperature. Boc-Tyr(Bzl)-OH (20 kg; Senn Chemicals, Switzerland) and HOBt (7.3 kg) were added as solids. A solution of DCC (12.2 kg) in DMF (40 L) was added to the mixture at −6° C. The completion of the reaction was monitored by TLC and HPLC.

Sources & evidence

ORD record
ord-88c1079705284816b8b872fb275efbf2
Source dataset
uspto-grants-2014_12
Patent number
US08921517B2

Reaction notes

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