Cyclopentanepropanoic acid → HCID 56994837, compound

HRID 1654310Notes

Reaction equation

HRID 1654310 reaction equation
[CH2:1]([NH:3][CH2:4][CH2:5][CH2:6][CH:7]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])=[CH:11][CH:10]=1)[OH:8])[CH3:2].[CH:20]1([CH2:25][CH2:26][C:27](O)=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]1>>[CH:20]1([CH2:25][CH2:26][C:27]([CH2:2][CH2:1][NH:3][CH2:4][CH2:5][CH2:6][CH:7]([C:9]2[CH:10]=[CH:11][C:12]([NH:15][S:16]([CH3:19])(=[O:17])=[O:18])=[CH:13][CH:14]=2)[OH:8])=[O:28])[CH2:24][CH2:23][CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 8818Cyclopentanepropanoic acidHCID 10779588N-(4-(4-(ethylamino)-1-hydroxybutyl)phenyl)methanesulfonamide

Product 1

HCID 56994837HCID 56994837, compoundYield 42.8%

Procedure

The product from Example 7, Step II was condensed with 3-cyclopentylpropionic acid according to Procedure E (Example 7, Step III). The product was recrystallized from EtOAc-hexane to give N-[4-[4-[(2-Cyclopentylethylcarbonyl)ethylamino]-1-hydroxybutyl]phenyl]methanesulfonamide (42.8%): mp 101°-102° C.; NMR (CDCl3) δ1.13 (m, 5H), 1.63 (m, 13H), 2.3 (m, 2H), 2.99 (d, 3H), 3.39 (m, 4H), 4.72 (m, 1H), 7.07 (s, 1H), 7.24 (m, 4H); MS m/z (relative intensity) 410 (M+, 2.8), 392 (3.2), 331 (11.5), 223 (29.0), 207 (6.3), 200 (2.9), 189 (19.4); IR (Nujol) 3397, 3190, 1591 cm-1. Anal. calc'd for C21H34N2O4S: C, 61.43 ; H, 8.35; N, 6.82; S, 7.81. Found: C, 61.21; H, 8.56; N, 6.59; S, 7.77.

Workup

  1. customThe product was recrystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-a250a68ec0214525afba6ea48158f217
Source dataset
uspto-grants-1995_04
Patent number
US05405997

Reaction notes

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