Hydrochloric Acid → (3S*,5R*)-5-(3,3-Dimethyl-butyrylamino)-piperidine-3-carboxylic acid cyclopropyl-(2,3-dichloro-benzyl)-amide

HRID 1698324Notes

Reaction equation

HRID 1698324 reaction equation
C1C2C(COC([N:18]3[CH2:23][C@@H:22]([C:24](=[O:38])[N:25]([CH:35]4[CH2:37][CH2:36]4)[CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=4[Cl:34])[CH2:21][C@@H:20]([NH2:39])[CH2:19]3)=O)C3C(=CC=CC=3)C=2C=CC=1.Cl.[C:41]([CH2:45][C:46](Cl)=[O:47])([CH3:44])([CH3:43])[CH3:42]>CC#N>[CH:35]1([N:25]([CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([Cl:33])[C:28]=2[Cl:34])[C:24]([C@H:22]2[CH2:21][C@@H:20]([NH:39][C:46](=[O:47])[CH2:45][C:41]([CH3:44])([CH3:43])[CH3:42])[CH2:19][NH:18][CH2:23]2)=[O:38])[CH2:36][CH2:37]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 815143,3-Dimethylbutanoyl chlorideHCID 69066294(3R*,5S*)-3-amino-5-[cyclopropyl-(2,3-dichloro-benzyl)-carbamoyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester

Product 1

HCID 15984734(3S*,5R*)-5-(3,3-Dimethyl-butyrylamino)-piperidine-3-carboxylic acid cyclopropyl-(2,3-dichloro-benzyl)-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-[cyclopropyl-(2,3-dichloro-benzyl)-carbamoyl]-piperidine-1-carboxylic acid 9H-fluoren-9-ylmethyl ester; hydrochloride and tert-butyl acetyl chloride. MS (LC-MS): 440.5/442.4 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.28 min.

Workup

  1. custom5.28 min.

Sources & evidence

ORD record
ord-91aa59567e6047e68370860dc4a11fbf
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

Loading…