4-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride → Methyl (S)-2-[4-(2-methylpropene-1-sulfonyl)piperazin-1-yl]-3-(4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino)propanoate

HRID 874593Notes

Reaction equation

HRID 874593 reaction equation
Cl.Cl.NC[C@H](N1CCN(S(CC(C)C)(=O)=O)CC1)C(OC)=O.Cl.CC1C=C(COC2C=CC(S(Cl)(=O)=O)=CC=2)C2C(=CC=CC=2)N=1.[CH3:47][CH:48]([CH3:88])[CH2:49][S:50]([N:53]1[CH2:58][CH2:57][N:56]([C@@H:59]([CH2:64][NH:65][S:66]([C:69]2[CH:74]=[CH:73][C:72]([O:75][CH2:76][C:77]3[C:86]4[C:81](=[CH:82][CH:83]=[CH:84][CH:85]=4)[N:80]=[C:79]([CH3:87])[CH:78]=3)=[CH:71][CH:70]=2)(=[O:68])=[O:67])[C:60]([O:62][CH3:63])=[O:61])[CH2:55][CH2:54]1)(=[O:52])=[O:51]>>[CH3:47][C:48]([CH3:88])=[CH:49][S:50]([N:53]1[CH2:54][CH2:55][N:56]([C@@H:59]([CH2:64][NH:65][S:66]([C:69]2[CH:70]=[CH:71][C:72]([O:75][CH2:76][C:77]3[C:86]4[C:81](=[CH:82][CH:83]=[CH:84][CH:85]=4)[N:80]=[C:79]([CH3:87])[CH:78]=3)=[CH:73][CH:74]=2)(=[O:67])=[O:68])[C:60]([O:62][CH3:63])=[O:61])[CH2:57][CH2:58]1)(=[O:52])=[O:51]

Participants

4

Reactant 3

HCID 866078654-(2-Methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochlorideHCID 86715684methyl (S)-3-amino-2-[4-(2-methylpropane-1-sulfonyl)piperazin-1-yl]propanoate dihydrochlorideHCID 86715687methyl (S)-2-[4-(2-methylpropane-1-sulfonyl)piperazin-1-yl]-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propanoate

Product 1

HCID 86715686Methyl (S)-2-[4-(2-methylpropene-1-sulfonyl)piperazin-1-yl]-3-(4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino)propanoate

Procedure

In a manner analogous to example 3.6, using 621 mg (1.6 mmol) of methyl (S)-3-amino-2-[4-(2-methylpropane-1-sulfonyl)piperazin-1-yl]propanoate dihydrochloride and 876 mg (2.3 mmol) of 4-(2-methylquinolin-4-ylmethoxy)benzenesulfonyl chloride hydrochloride (prepared as described in example 17.2), 643 mg (64%) of methyl (S)-2-[4-(2-methylpropane-1-sulfonyl)piperazin-1-yl]-3-[4-(2-methylquinolin-4-ylmethoxy)benzenesulfonylamino]propanoate are obtained in the form of an oil.

Workup

  1. customare obtained in the form of an oil

Sources & evidence

ORD record
ord-9f5ab65d5fb2404a9afbc2d9ffcc5c53
Source dataset
uspto-grants-2015_03
Patent number
US08980897B2

Reaction notes

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