2-(R)-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propionic acid, benzyl ester → 2-(R)-(3-(S)-(4-(N-((2-Chloro-4-fluorobenzyl)carbonyl)-N-ethylamino)-piperidin-1 yl)methyl-4-(S)-phenyl-pyrrolidin-1-yl)-3-(cyclobutyl)propionic acid

HRID 2185546Notes

Reaction equation

HRID 2185546 reaction equation
[CH:1]([C@@H:3]1[C@@H:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][N:5]([C@H:14]([CH2:25][CH:26]2[CH2:29][CH2:28][CH2:27]2)[C:15]([O:17]CC2C=CC=CC=2)=[O:16])[CH2:4]1)=O.FC(F)(F)C(O)=O.[Cl:37][C:38]1[CH:55]=[C:54]([F:56])[CH:53]=[CH:52][C:39]=1[CH2:40][C:41]([N:43]([CH:46]1[CH2:51][CH2:50][NH:49][CH2:48][CH2:47]1)[CH2:44][CH3:45])=[O:42]>>[Cl:37][C:38]1[CH:55]=[C:54]([F:56])[CH:53]=[CH:52][C:39]=1[CH2:40][C:41]([N:43]([CH:46]1[CH2:51][CH2:50][N:49]([CH2:1][C@@H:3]2[C@@H:7]([C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH2:6][N:5]([C@H:14]([CH2:25][CH:26]3[CH2:27][CH2:28][CH2:29]3)[C:15]([OH:17])=[O:16])[CH2:4]2)[CH2:48][CH2:47]1)[CH2:44][CH3:45])=[O:42]

Participants

3

Reactant 2

HCID 599245802-(R)-(3-(R)-Formyl-4-(S)-phenylpyrrolidin-1-yl)-3-(cyclobutyl)propionic acid, benzyl esterHCID 701773494-(N-((2-chloro-4-fluorobenzyl)carbonyl)-N-ethylamino)piperidine trifluoroacetate

Product 1

HCID 213410852-(R)-(3-(S)-(4-(N-((2-Chloro-4-fluorobenzyl)carbonyl)-N-ethylamino)-piperidin-1 yl)methyl-4-(S)-phenyl-pyrrolidin-1-yl)-3-(cyclobutyl)propionic acidYield 15%

Procedure

The title compound was prepared from 2-(R)-(3-(R)-formyl-4-(S)-phenyl-pyrrolidin-1-yl)-3-(cyclobutyl)propionic acid, benzyl ester (25 mg, 0.07 mmol, Aldehyde 1) and 4-(N-((2-chloro-4-fluorobenzyl)carbonyl)-N-ethylamino)piperidine trifluoroacetate (41 mg, 0.1 mmol, from Example 14 , Step A) according to the method described in Example 14 , Step B to give 6.0 mg (15%) of the title compound. ESI-MS: 584.3 (M+H); HPLC A: 2.70 min.

Sources & evidence

ORD record
ord-665e2334d3ae415d9843d52661a45b3b
Source dataset
uspto-grants-2002_06
Patent number
US06399619B1

Reaction notes

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