Leucinamide → N-(tert-Butoxycarbonyl)-L-phenylalanyl-L-leucinamide

HRID 2380565Notes

Reaction equation

HRID 2380565 reaction equation
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:20][C@H:21]([C:26]([NH2:28])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24]>CS(C)=O>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@H:2]([C:10]([NH:20][C@H:21]([C:26]([NH2:28])=[O:27])[CH2:22][CH:23]([CH3:25])[CH3:24])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 69640LeucinamideHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-

Product 1

HCID 15030956N-(tert-Butoxycarbonyl)-L-phenylalanyl-L-leucinamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

1 ml 0.1M veronal-Na/HCl buffer, pH 8.3/50% (v/v) DMSO, containing 100 mM Boc-Phe-OCam, 300 mM H-Leu-NH2 and 100 μM trypsinogen is agitated at room temperature under pH control. After 3 hours, the reaction is stopped as described in Example 3. The yield is analytically determined with HPLC to be 93% of theory.

Sources & evidence

ORD record
ord-8c0a42b33beb437d98f0b9d43cf70277
Source dataset
uspto-grants-1994_11
Patent number
US05369018

Reaction notes

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