Hydrochloric Acid → HCID 23587465, compound

HRID 489213Notes

Reaction equation

HRID 489213 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH:7]2[CH2:12][CH2:11][N:10]([C@@H:13]3[CH2:17][C@@H:16]([OH:18])[CH2:15][C@H:14]3[NH:19][C:20]([NH:22][C:23]3[CH:28]=[C:27]([O:29][CH3:30])[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=3)=[O:21])[CH2:9][CH2:8]2)=[CH:4][CH:3]=1.Cl.CCOCC>C(Cl)Cl>[ClH:1].[Cl:1][C:2]1[CH:36]=[CH:35][C:5]([CH2:6][CH:7]2[CH2:8][CH2:9][N:10]([C@@H:13]3[CH2:17][C@@H:16]([OH:18])[CH2:15][C@H:14]3[NH:19][C:20]([NH:22][C:23]3[CH:24]=[C:25]([O:33][CH3:34])[C:26]([O:31][CH3:32])=[C:27]([O:29][CH3:30])[CH:28]=3)=[O:21])[CH2:11][CH2:12]2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 23587461HCID 23587461, compound

Product 1

HCID 23587465HCID 23587465, compoundYield 198.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (±)-1-{(1R,2R,4S)-2-[4-(4-chlorobenzyl)piperidin-1-yl]-4-hydroxy-cyclopentyl}-3-(3,4,5-trimethoxyphenyl)urea (102 mg, 0.20 mmol) in CH2Cl2 was treated with 1 N HCl in Et2O (0.5 mL, 0.5 mmol) and concentrated to give the product (110 mg, 100%) as a yellow solid: mp 137.0-143.0° C.; IR 3405 (br), 2935, 1685, 1606, 1554, 1507 cm−1; 1H NMR [(CD3)2SO] δ 1.48-2.12 (m, 11H), 2.54 (m, 2H), 2.90 (m, 2H), 3.45 (m, 1H), 3.58 (s, 3H), 3.71 (s, 6H), 4.22 (m, 1H), 4.48 (m, 1H), 5.16 (br s, 1H), 6.42 (d, J=9.4 Hz, 1H), 6.70 (s, 2H), 7.21 (m, 2H), 7.34 (m, 2H), 10.19 (br s, 1H); MS m/z 518 (M+H)+.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-660dc160b20747eda366b4b68e0729d3
Source dataset
uspto-grants-2005_12
Patent number
US06977265B2

Reaction notes

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