Acetyl chloride → HCID 12970146, compound

HRID 458009Notes

Reaction equation

HRID 458009 reaction equation
[N+:1]([CH2:4][C:5]1([CH2:11][CH2:12][NH2:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)([O-:3])=[O:2].[C:14](Cl)(=[O:16])[CH3:15].C(N(CC)CC)C>O1CCCC1>[N+:1]([CH2:4][C:5]1([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 12970145HCID 12970145, compound2×

Product 1

HCID 12970146HCID 12970146, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The amine hydrochloride salt (compound 4, 0.50 g, 2.25 mmol) was reacted with acetyl chloride (0.20 g, 2.55 mmol) and triethylamine (0.45 g, 4.45 mmol) in tetrahydrofuran following the procedure described in Example 1, Step 4. Purification by chromatography on silica eluting with ethyl acetate gave the required product as a crystalline solid (0.35 g, 69%); mp 68–70° C.

Workup

  1. customPurification by chromatography on silica eluting with ethyl acetate

Sources & evidence

ORD record
ord-b0a909a326704d49b2e66b3996699bec
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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