Acetyl chloride → HCID 89620183, compound

HRID 1500811Notes

Reaction equation

HRID 1500811 reaction equation
Cl.Cl.Cl.[NH2:4][C:5]1[C:10]2=[C:11]([C:29]3[S:30][C:31]4[C:37]([O:38][CH3:39])=[CH:36][C:35]([CH3:40])=[CH:34][C:32]=4[CH:33]=3)[C:12]([CH2:21][N:22]3[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]3)=[C:13]([CH2:14][N:15]3[CH2:20][CH2:19][NH:18][CH2:17][CH2:16]3)[N:9]2[N:8]=[CH:7][N:6]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:47](Cl)(=[O:49])[CH3:48]>ClCCl.C1COCC1>[C:47]([N:18]1[CH2:17][CH2:16][N:15]([CH2:14][C:13]2[N:9]3[C:10]([C:5]([NH2:4])=[N:6][CH:7]=[N:8]3)=[C:11]([C:29]3[S:30][C:31]4[C:37]([O:38][CH3:39])=[CH:36][C:35]([CH3:40])=[CH:34][C:32]=4[CH:33]=3)[C:12]=2[CH2:21][N:22]2[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]2)[CH2:20][CH2:19]1)(=[O:49])[CH3:48]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 131734278HCID 131734278, compound

Product 1

HCID 89620183HCID 89620183, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A suspension of Example 49 (310 mg, 522 μmol) in dichloromethane/THF (2.5:1, 9.64 ml) was treated with sodium carbonate (442 mg, 4.17 mmol) and stirred at rt for 30 min. Acetyl chloride (74 μl, 1.04 mmol) was added, and the resulting mixture was stirred at rt for 2 h. After quenching with methanol, the mixture was evaporated, and the residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid) affording 133 mg (45% of th.) of the title compound.

Workup

  1. stirringthe resulting mixture was stirred at rt for 2 h
  2. customAfter quenching with methanol
  3. customthe mixture was evaporated
  4. customthe residue was purified by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid)

Sources & evidence

ORD record
ord-bdf1fa7daccf462e90ab31d4913e4e0e
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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