1,2-Dichloroethane → HCID 23521315, compound

HRID 392031Notes

Reaction equation

HRID 392031 reaction equation
[F:1][CH2:2][C:3](=[O:34])[CH:4]([NH:9][C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[C:18]([N:20]1[C:33]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[S:27][C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:19])=[O:11])[CH2:5][C:6]([OH:8])=O.C(Cl)CCl.[CH2:39]([NH2:41])[CH3:40]>C(Cl)Cl.C1COCC1>[CH2:39]([NH:41][C:6](=[O:8])[CH2:5][CH:4]([NH:9][C:10]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][N:13]1[C:18]([N:20]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=2[S:27][C:28]2[C:33]1=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:19])=[O:11])[C:3](=[O:34])[CH2:2][F:1])[CH3:40]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 6341EthylamineHCID 10184630HCID 10184630, compound

Product 1

HCID 23521315HCID 23521315, compoundYield 11%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred mixture of [3S/R, (2S)]-5-fluoro-4-oxo-3-{[1-(phenothiazine-10-carbonyl)piperidine-2-carbonyl]amino}-pentanoic acid (196 mg, 0.4 mmol), prepared as in Example 1, in anhydrous DCM (8 ml), was added Polymer bound EDC (400 mg, 0.8 mmol) and a solution of the ethylamine in THF (0.6 ml of a 2M solution, 12 mmol). The mixture was stirred at room temperature for 16 h then concentrated under reduced pressure. The residue was purified by flash chromatography (2.5% methanol in dichloromethane) to afford the title compound as a white solid (22.7 mg, 11%): 1H NMR (400 MHz, CDCl3) δ 1.09-1.39 (3H, m), 1.44-1.66 (6H, m), 2.04-3.66 (7H, m), 4.18-4.76 (6H, m) and 7.10-7.79 (8H, m). 19F NMR (376 MHz, CDC3) δ −223.32, −223.73, −225.92 and −226.76.

Workup

  1. concentrationthen concentrated under reduced pressure
  2. customThe residue was purified by flash chromatography (2.5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-75302edebda24a1b8948aef6f6022a7d
Source dataset
uspto-grants-2004_10
Patent number
US06800619B2

Reaction notes

Loading…