1-(Bromomethyl)naphthalene → Methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(naphthalen-1-ylmethoxy)benzoylamino]propanoate

HRID 517512Notes

Reaction equation

HRID 517512 reaction equation
OC1C=CC(C(NC[C@H](N2CCN(S(C)(=O)=O)CC2)C(OC)=O)=O)=CC=1.BrCC1C2C(=CC=CC=2)C=CC=1.[CH3:39][S:40]([N:43]1[CH2:48][CH2:47][N:46]([C@@H:49]([CH2:54][NH:55][C:56](=[O:76])[C:57]2[CH:62]=[CH:61][C:60]([O:63][CH2:64][C:65]3[C:74]4[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=4)N=[C:67]([CH3:75])[CH:66]=3)=[CH:59][CH:58]=2)[C:50]([O:52][CH3:53])=[O:51])[CH2:45][CH2:44]1)(=[O:42])=[O:41]>>[CH3:39][S:40]([N:43]1[CH2:48][CH2:47][N:46]([C@@H:49]([CH2:54][NH:55][C:56](=[O:76])[C:57]2[CH:58]=[CH:59][C:60]([O:63][CH2:64][C:65]3[C:74]4[C:69](=[CH:70][CH:71]=[CH:72][CH:73]=4)[CH:75]=[CH:67][CH:66]=3)=[CH:61][CH:62]=2)[C:50]([O:52][CH3:53])=[O:51])[CH2:45][CH2:44]1)(=[O:41])=[O:42]

Participants

4

Reactant 3

HCID 1378441-(Bromomethyl)naphthaleneHCID 67056914methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoateHCID 86667909methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(2-methylquinolin-4-ylmethoxy)benzoylamino]-propanoate

Product 1

HCID 86667908Methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(naphthalen-1-ylmethoxy)benzoylamino]propanoate

Procedure

In a manner similar to example 4-5, starting from 300 mg (0.8 mmol) of methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)-propanoate (prepared as described in example 4-4) and from 200 mg (1.2 mmol) of 1-bromomethylnaphthalene, 320 mg (78%) of methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(2-methylquinolin-4-ylmethoxy)benzoylamino]-propanoate are obtained in the form of a white solid.

Workup

  1. customare obtained in the form of a white solid

Sources & evidence

ORD record
ord-41dcbb00c1ac4f79b59412b095c5e65e
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

Loading…