Diethylamine → HCID 23521309, compound

HRID 392032Notes

Reaction equation

HRID 392032 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.N=C=N.[CH2:38]([NH:40][CH2:41][CH3:42])[CH3:39]>C(Cl)Cl>[CH2:38]([N:40]([CH2:41][CH3:42])[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])[CH3:39]

Participants

5

Reactant 3

HCID 8021DiethylamineHCID 160435CarbodiimideHCID 10184630HCID 10184630, compound

Product 1

HCID 23521309HCID 23521309, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of [3S/R, (2S)]-5-fluoro-4-oxo-3-{[1-(phenothiazine-10-carbonyl)piperidine-2-carbonyl]amino}-pentanoic acid (200 mg, 0.4 mmol), prepared as in Example 1, in anhydrous DCM (4 ml), was added carbodiimide (74 mg, 0.44 mmol) and a diethylamine (0.62 ml, 6 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 (25.3 mg, 11%): 1H NMR (400 MHz, CDCl3) δ 1.00-1.23 (6H, m), 1.45-1.67 (6H, m), 2.18 (1H, m), 2.74 (1H, m), 2.92 (1H, m), 3.21-3.33 (4H,m), 3.65 (1H, m), 4.68 (1H, m), 4.85 (1H, m), 4.98-5.36 (2H, m) and 7.12-7.95 (8H, m). 19F NMR (376 MHz, CDCl3) δ −232.37 and −232.72.

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-e4bc25e1b18b4219b2b665672aaed584
Source dataset
uspto-grants-2004_10
Patent number
US06800619B2

Reaction notes

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