Dicyclohexylcarbodiimide → (5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetyl Methanesulfonamide

HRID 11645

Reaction equation

HRID 11645 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[C:6]([CH:13]=1)[CH2:7][O:8][CH2:9][C:10](O)=[O:11].[CH:34]1(N=C=NC2CCCCC2)CCCCC1.C[S:50]([NH2:53])(=[O:52])=[O:51]>ClCCl.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:14][CH2:15][C:16]([N:18]2[CH2:23][C@H:22]([CH3:24])[N:21]([CH2:25][C:26]3[CH:27]=[CH:28][C:29]([F:32])=[CH:30][CH:31]=3)[CH2:20][C@H:19]2[CH3:33])=[O:17])=[C:6]([CH:13]=1)[CH2:7][O:8][CH:9]([C:10](=[O:11])[CH3:34])[S:50]([NH2:53])(=[O:52])=[O:51]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 72879MethanesulfonamideHCID 69655258(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetic Acid

Product 1

HCID 86591164(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetyl MethanesulfonamideYield 36.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzyloxy)-acetic acid (0.11 g, 0.22 mmol) in dichloromethane (10 mL) was added 4-dimethylaminopyridine (0.04 g, 0.33 mmol) and 1,3-dicyclohexylcarbodiimide (0.049 g, 0.24 mmol). The resulting reaction mixture was stirred at ambient temperature for 20 minutes and then treated with methanesulfonamide (0.025 g, 0.26 mmol). The reaction was stirred at ambient temperature for 18 hours, filtered through a pad of celite and the resulting filter cake was washed with dichloromethane. The combined organics were concentrated in vacuo and purified via chromatography on silica gel to give the title compound (0.045 g, LRMS: 556.2).

Workup

  1. customThe resulting reaction mixture
  2. stirringThe reaction was stirred at ambient temperature for 18 hours
  3. filtrationfiltered through a pad of celite
  4. filtrationthe resulting filter cake
  5. washwas washed with dichloromethane
  6. concentrationThe combined organics were concentrated in vacuo
  7. custompurified via chromatography on silica gel

Sources & evidence

ORD record
ord-19342639db9b4a3ba8c49da68878b3f5
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

Loading…