Diisopropylethylamine → HCID 58746725, compound

HRID 724644Notes

Reaction equation

HRID 724644 reaction equation
[NH2:1][C@@H:2]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([CH:29]2[S:33](=[O:35])(=[O:34])[NH:32][C:31](=[O:36])[CH2:30]2)=[CH:25][CH:24]=1)[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:12]=1[C:13]([O:15][CH3:16])=[O:14])=[O:4].C(N(CC)C(C)C)(C)C.[CH3:46][O:47][C:48](=[O:60])[C@@H:49]([N:57]=[C:58]=[O:59])[CH2:50][C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CN(C)C=O>[CH2:50]([C@@H:49]([C:48](=[O:60])[O:47][CH3:46])[NH:57][C:58](=[O:59])[NH:1][C@@H:2]([CH2:22][C:23]1[CH:24]=[CH:25][C:26]([CH:29]2[S:33](=[O:35])(=[O:34])[NH:32][C:31](=[O:36])[CH2:30]2)=[CH:27][CH:28]=1)[C:3](=[O:4])[NH:5][CH2:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:20]=[CH:19][CH:18]=[C:17]([OH:21])[C:12]=1[C:13]([O:15][CH3:16])=[O:14])[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 1514293Methyl N-(oxomethylidene)phenylalaninateHCID 69597926HCID 69597926, compound

Product 1

HCID 58746725HCID 58746725, compoundYield 17.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 2-[4-({(2S)-2-amino-3-[4-(1,1-dioxido-3-oxoisothiazolidin-5-yl)phenyl]propanoyl}amino)butoxy]-6-hydroxybenzoate (8.0 mg, 0.015 mmol) in N,N-dimethylformamide (0.5 mL) was added N,N-diisopropylethylamine (0.008 mL, 0.045 mmol) and (S)-2-isocyanato-3-phenyl-propionic acid methyl ester (3.5 mg, 0.017 mmol) and stirred overnight at room temperature. The product was purified by preparative LCMS to afford the desired product (1.9 mg, 17%). LCMS found for C35H41N4O11S (M+H)+: m/z=725.1

Workup

  1. customThe product was purified by preparative LCMS

Sources & evidence

ORD record
ord-953ea17595214b639371ab8e83627051
Source dataset
uspto-grants-2006_11
Patent number
US07141596B2

Reaction notes

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