3,3-Dimethylbutanoyl chloride → N-[N-[N-(3,3-dimethylbutyryl)-L-leucyl]-D-tryptophanyl]-beta-alanine ethyl ester

HRID 2295173Notes

Reaction equation

HRID 2295173 reaction equation
[NH2:1][C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].FC(C(O)=O)(F)F.[CH3:38][C:39]([CH3:45])([CH3:44])[CH2:40][C:41](Cl)=[O:42]>N1C=CC=CC=1>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][CH2:24][NH:23][C:21](=[O:22])[C@@H:10]([CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[NH:9][C:7](=[O:8])[C@H:2]([CH2:3][CH:4]([CH3:5])[CH3:6])[NH:1][C:41](=[O:42])[CH2:40][C:39]([CH3:45])([CH3:44])[CH3:38])[CH3:30]

Participants

4

Reactant 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 131719107Leu-DTrp-betaAla-OEt-TFA

Product 1

HCID 54526361N-[N-[N-(3,3-dimethylbutyryl)-L-leucyl]-D-tryptophanyl]-beta-alanine ethyl ester

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of Leu-DTrp-βAla-OEt.TFA (33.0 mg) obtained in Example 51-(1) in pyridine (0.5 ml) was added 3,3-dimethylbutyryl chloride (12.8 ml) at 0° C. under nitrogen. The reaction mixture was stirred for 10 min, quenched with water (0.1 ml), and concentrated under reduced pressure. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=15/1 for development to give the product (21.8 mg).

Workup

  1. customquenched with water (0.1 ml)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=15/1 for development

Sources & evidence

ORD record
ord-546ac5a1b77a4d058517cad3ca08fbdf
Source dataset
uspto-grants-1997_11
Patent number
US05691315

Reaction notes

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