Ethyl 4-piperidinecarboxylate → (S)-1-{2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propionyl}piperidine-4-carboxylic acid ethyl ester

HRID 271849Notes

Reaction equation

HRID 271849 reaction equation
[C:1]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C@@H:16]([CH2:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH3:44])[C:34]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:35])[CH:28]=2)=[CH:23][CH:22]=1)[C:17](O)=[O:18])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:45]1[CH2:50][CH2:49][CH:48]([C:51]([O:53][CH2:54][CH3:55])=[O:52])[CH2:47][CH2:46]1>>[CH2:54]([O:53][C:51]([CH:48]1[CH2:49][CH2:50][N:45]([C:17](=[O:18])[C@@H:16]([NH:15][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:20][C:21]2[CH:26]=[CH:25][C:24]([C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([N:33]([CH3:44])[C:34]([NH:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])=[O:35])[CH:28]=3)=[CH:23][CH:22]=2)[CH2:46][CH2:47]1)=[O:52])[CH3:55]

Participants

3

Reactant 2

HCID 70770Ethyl 4-piperidinecarboxylateHCID 10483579(S)-2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl)propionic acid

Product 1

HCID 10010169(S)-1-{2-(2-benzoylphenylamino)-3-[3'-(3-heptyl-1-methylureido)biphenyl-4-yl]propionyl}piperidine-4-carboxylic acid ethyl esterYield 107.7%

Procedure

In a similar manner, using 20 mg (33.8 μmol) of the (S)-2-(2-benzoylphenylamino)-3-[3′-(3-heptyl-1-methylureido)biphenyl-4-yl]propionic acid (Example 2) and 4.8 mg (30.5 μmol) of ethyl piperidine-4-carboxylate, 24 mg of expected product are obtained with a quantitative yield.

Sources & evidence

ORD record
ord-adf664b9e95d471ba98ba3c74d900e6e
Source dataset
uspto-grants-2008_11
Patent number
US07452878B2

Reaction notes

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