Ethyl 2-oxocyclohexanecarboxylate → ethyl (S)-2-(2-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-1-ethoxycarbonylethylamino)-benzoate

HRID 271855Notes

Reaction equation

HRID 271855 reaction equation
C(C1C=CC=CC=1N[C@@H](CC1C=CC(C2C=CC=C(NC)C=2)=CC=1)C(OCC)=O)(=O)C1C=CC=CC=1.[NH2:37][C@@H:38]([CH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]2[CH:56]=[CH:55][CH:54]=[C:53]([CH2:57][NH:58][CH2:59][C:60](=[O:67])[C:61]3[CH:66]=[CH:65][CH:64]=[CH:63][CH:62]=3)[CH:52]=2)=[CH:47][CH:46]=1)[C:39]([O:41][CH2:42][CH3:43])=[O:40].O=[C:69]1[CH2:74][CH2:73][CH2:72][CH2:71][CH:70]1[C:75]([O:77][CH2:78][CH3:79])=[O:76]>>[C:60]([CH2:59][NH:58][CH2:57][C:53]1[CH:52]=[C:51]([C:48]2[CH:47]=[CH:46][C:45]([CH2:44][C@H:38]([NH:37][C:71]3[CH:72]=[CH:73][CH:74]=[CH:69][C:70]=3[C:75]([O:77][CH2:78][CH3:79])=[O:76])[C:39]([O:41][CH2:42][CH3:43])=[O:40])=[CH:50][CH:49]=2)[CH:56]=[CH:55][CH:54]=1)(=[O:67])[C:61]1[CH:62]=[CH:63][CH:64]=[CH:65][CH:66]=1

Participants

4

Reactant 3

HCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 69685584ethyl (S)-2-(2-benzoylphenylamino)-3-(3'-methylaminobiphenyl-4-yl)propionateHCID 69685681ethyl (S)-2-amino-3-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}propionate

Product 1

HCID 69685636ethyl (S)-2-(2-{3'-[(benzoylmethylamino)methyl]biphenyl-4-yl}-1-ethoxycarbonylethylamino)-benzoateYield 10%

Procedure

In a manner similar to the preparation of the ethyl (S)-2-(2-benzoylphenylamino)-3-(3′-methylaminobiphenyl-4-yl)propionate (Example 1 g), using 6.7 g (16.1 mmol) of ethyl (S)-2-amino-3-{3′-[(benzoylmethyl-amino)methyl]biphenyl-4-yl}propionate (Example 28f) and 3 ml (19.3 mmol) of ethyl 2-oxocyclohexanecarboxylate, 0.90 g of ethyl (S)-2-(2-{3′-[(benzoylmethylamino)methyl]biphenyl-4-yl}-1-ethoxycarbonylethylamino)-benzoate is isolated with a 10% yield.

Sources & evidence

ORD record
ord-e13f4fb616ff43d2809d7a60f12c809a
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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