Acetyl chloride → HCID 67071625, compound

HRID 874267Notes

Reaction equation

HRID 874267 reaction equation
[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([C:18]([O:20]C(C)(C)C)=O)[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29].[C:31](Cl)(=O)C.CCN(C(C)C)C(C)C>C(Cl)Cl>[CH3:1][O:2][C:3](=[O:30])/[CH:4]=[CH:5]/[C:6]1[CH:7]=[C:8]2[C:26](=[CH:27][CH:28]=1)[O:25][C:11]1([CH2:17][CH2:16][CH2:15][N:14]([C:18](=[O:20])[CH3:31])[CH2:13][CH2:12]1)[CH2:10][C:9]2=[O:29]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67071624HCID 67071624, compound2×

Product 1

HCID 67071625HCID 67071625, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of (±)-(E)-3-[4-oxo-spiro(chromane-2,4′-azepane)-6-yl]acrylic acid methyl ester hydrochloride salt (500 mg, 1.43 mmol, Intermediate 3) in DCM (15 ml) was treated with acetyl chloride (0.121 ml, 1.72 mmol) and DIPEA (0.507 ml, 2.86 mmol) and was stirred at RT for 1. The solution was evaporated under vacuum and the crude product was purified by chromatography column (eluent: DCM/MeOH 95:5) to give (±)-(E)-3-[1′-acetyl-4-oxo-spiro(chromane-2,4′-azepane)-6-yl]-acrylic acid methyl ester (503 mg).

Workup

  1. customThe solution was evaporated under vacuum
  2. customthe crude product was purified by chromatography column (eluent: DCM/MeOH 95:5)

Sources & evidence

ORD record
ord-3ca56ae444fa41b1b648a2c2356f649c
Source dataset
uspto-grants-2015_03
Patent number
US08980877B2

Reaction notes

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