Acetyl chloride → HCID 89620461, compound

HRID 1500809Notes

Reaction equation

HRID 1500809 reaction equation
[NH2:1][C:2]1[C:7]2=[C:8]([C:24]3[S:25][C:26]4[C:32]([O:33][CH3:34])=[CH:31][C:30]([CH3:35])=[CH:29][C:27]=4[CH:28]=3)[C:9]([CH2:18][O:19][CH2:20][C:21]([NH2:23])=[O:22])=[C:10]([CH2:11][N:12]3[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]3)[N:6]2[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[Na+].[Na+].[C:42](Cl)(=[O:44])[CH3:43]>C1COCC1.ClCCl>[C:42]([N:15]1[CH2:14][CH2:13][N:12]([CH2:11][C:10]2[N:6]3[C:7]([C:2]([NH2:1])=[N:3][CH:4]=[N:5]3)=[C:8]([C:24]3[S:25][C:26]4[C:32]([O:33][CH3:34])=[CH:31][C:30]([CH3:35])=[CH:29][C:27]=4[CH:28]=3)[C:9]=2[CH2:18][O:19][CH2:20][C:21]([NH2:23])=[O:22])[CH2:17][CH2:16]1)(=[O:44])[CH3:43]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 10340Sodium CarbonateHCID 71612249HCID 71612249, compound

Product 1

HCID 89620461HCID 89620461, compound

Reagents, catalysts & solvents 1

HCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

A solution of Example 33 (105 mg, 68% purity, 144 μmol) in THF/dichloromethane (1:2.5, 3.9 ml) was treated with sodium carbonate (179 mg, 1.6 mmol) and stirred at rt for 30 min. Acetyl chloride (30 μl, 424 μmol) was added, and the resulting mixture was stirred at rt for 30 min, then quenched with methanol (2 ml) and evaporated. Purification by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid) afforded 30 mg (85% purity, 34% of th.) of the title compound.

Workup

  1. stirringthe resulting mixture was stirred at rt for 30 min
  2. customquenched with methanol (2 ml)
  3. customevaporated
  4. customPurification by preparative RP-HPLC (Reprosil C18, gradient 10-95% acetonitrile/0.1% aq. formic acid)

Sources & evidence

ORD record
ord-e59364938b134273aa8d2b778402fa7c
Source dataset
uspto-grants-2015_12
Patent number
US09206184B2

Reaction notes

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