HCID 69623856, compound → HCID 69623693, compound

HRID 890929Notes

Reaction equation

HRID 890929 reaction equation
[CH2:1]([S:4]([NH:7][C@@H:8]([C:13]([NH:15][C@H:16]([C:27]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][C:34]([C:37]#[N:38])=[CH:33][CH:32]=1)=[O:28])[CH2:17][N:18](C(OC(C)(C)C)=O)[CH3:19])=[O:14])[C@@H:9]([CH2:11][CH3:12])[CH3:10])(=[O:6])=[O:5])[CH2:2][CH3:3]>FC(F)(F)C(O)=O>[CH2:1]([S:4]([NH:7][C@@H:8]([C:13]([NH:15][C@H:16]([C:27]([NH:29][CH2:30][C:31]1[CH:32]=[CH:33][C:34]([C:37]#[N:38])=[CH:35][CH:36]=1)=[O:28])[CH2:17][NH:18][CH3:19])=[O:14])[C@@H:9]([CH2:11][CH3:12])[CH3:10])(=[O:6])=[O:5])[CH2:2][CH3:3]

Participants

3

Reactant 1

HCID 69623856HCID 69623856, compound

Product 1

HCID 69623693HCID 69623693, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To N-(propylsulfonyl)-D-isoleucyl-3-[(t-butoxycarbonyl)(methyl)amino]-N1-(4-cyanobenzyl)-L-alaninamide (1.6 g, 3 mmol), trifluoroacetic acid (10 ml) was added and stirred at room temperature under a nitrogen stream. After 1 hour, the reaction mixture was concentrated under reduced pressure and the residue was applied to column chromatography (Fuji Silysia NH-DM-1020; mobile phase: dichloromethane:methanol=1:0, 4:1) to give N-(propylsulfonyl)-D-isoleucyl-3-(methylamino)-N1-(4-cyanobenzyl)-L-alaninamide (1.3 g, 2.9 mmol; yield 96%).

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-3aba2bfe6bd649b390fd4068bc5b1f18
Source dataset
uspto-grants-2006_02
Patent number
US07001887B2

Reaction notes

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