Isobutyryl chloride → (3S*,5R*)-5-Isobutyrylamino-piperidine-3-carboxylic acid [4-chloro-3-(3-methoxy-propoxy)-benzyl]-cyclopropyl-amide

HRID 1698314Notes

Reaction equation

HRID 1698314 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.[C:46](Cl)(=[O:50])[CH:47]([CH3:49])[CH3:48]>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]([C@H:23]2[CH2:22][C@@H:21]([NH:45][C:46](=[O:50])[CH:47]([CH3:49])[CH3:48])[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 62325Isobutyryl 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 57870347(3S*,5R*)-5-Isobutyrylamino-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 isobutyryl chloride. MS: 466.4 [M+H]+; tR (HPLC, Nucleosil C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 8 min, flow 1.5 ml/min): 5.04 min.

Workup

  1. custom5.04 min.

Sources & evidence

ORD record
ord-3a0186648134459ab5e7cf5e1a4ae75b
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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