Cyclobutanecarbonyl chloride → 5-(Cyclobutanecarbonyl-amino)-piperidine-3-carboxylic acid [4-chloro-3-(3-methoxy-propoxy)-benzyl]-cyclopropyl-amide

HRID 1698313Notes

Reaction equation

HRID 1698313 reaction equation
Cl.C1C2C(COC([N:19]3[CH2:24][C@@H:23]([C:25](=[O:44])[N:26]([CH2:30][C:31]4[CH:36]=[CH:35][C:34]([Cl:37])=[C:33]([O:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43])[CH:32]=4)[CH:27]4[CH2:29][CH2:28]4)[CH2:22][C@@H:21]([NH2:45])[CH2:20]3)=O)C3C(=CC=CC=3)C=2C=CC=1.[CH:46]1([C:50](Cl)=[O:51])[CH2:49][CH2:48][CH2:47]1>CC#N>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:26]([CH:27]2[CH2:29][CH2:28]2)[C:25]([CH:23]2[CH2:22][CH:21]([NH:45][C:50]([CH:46]3[CH2:49][CH2:48][CH2:47]3)=[O:51])[CH2:20][NH:19][CH2:24]2)=[O:44])=[CH:32][C:33]=1[O:38][CH2:39][CH2:40][CH2:41][O:42][CH3:43]

Participants

4

Reactant 2

HCID 78705Cyclobutanecarbonyl chlorideHCID 131729669(3R*,5S*)-3-amino-5-{[4-chloro-3-(3-methoxy-propoxy)-benzyl]-cyclopropyl-carbamoyl}-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester, hydrochloride

Product 1

HCID 672731005-(Cyclobutanecarbonyl-amino)-piperidine-3-carboxylic acid [4-chloro-3-(3-methoxy-propoxy)-benzyl]-cyclopropyl-amide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound is prepared analogously as described in Example 61 using (3R*,5S*)-3-amino-5-{[4-chloro-3-(3-methoxy-propoxy)-benzyl]-cyclopropyl-carbamoyl}piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester, hydrochloride (Example 92A.) and cyclobutanecarbonyl chloride. MS: 478.4 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 4.97 min.

Workup

  1. custom4.97 min.

Sources & evidence

ORD record
ord-6ebe367ebe6d48dcbbc21602ed838719
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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