Acetyl chloride → HCID 12970146, compound

HRID 722839Notes

Reaction equation

HRID 722839 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-52aa2fca3db544afbcb2282bc809064c
Source dataset
uspto-grants-2006_11
Patent number
US07138542B2

Reaction notes

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