Acetyl chloride → HCID 10221648, compound

HRID 2184406Notes

Reaction equation

HRID 2184406 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][CH2:6][CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2([OH:27])[CH2:19][CH2:18][CH2:17][CH:16]2[NH:20][S:21]([CH:24]([CH3:26])[CH3:25])(=[O:23])=[O:22])=[CH:11][CH:10]=1.C(N(CC)CC)C>C(Cl)Cl>[OH:27][C:15]1([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:7][CH2:6][NH:5][C:1](=[O:3])[CH3:2])=[CH:10][CH:11]=2)[CH2:19][CH2:18][CH2:17][CH:16]1[NH:20][S:21]([CH:24]([CH3:25])[CH3:26])(=[O:23])=[O:22]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 22476606HCID 22476606, compound

Product 1

HCID 10221648HCID 10221648, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a 100 mL 3 neck flask fitted with a stirrer and thermometer, acetyl chloride (63 mg, 1.2 eq) is added dropwise to {2-[4-(2-aminoethoxy)phenyl]-2-hydroxycyclopentyl}[(methylethyl)sulfonyl]amine (230 mg, 0.67 mmol) and triethylamine (102 mg, 1.5 eq) in CH2Cl2 (40 mL) while stirring at 0° C. under a nitrogen atmosphere. The reaction is allowed to warm to room temperature and stirred for 2 hours. The reaction is then diluted with CH2Cl2 (50 mL) and the organic layer is washed two times with H2O, dried over Na2SO4, filtered, and concentrated under reduced vacuum to yield the product. This material is purified via silica gel chromatography employing the Chromatotron® and using 2000 micron rotor while eluting with a suitable eluent, such as hexanes/ethyl acetate to provide the title compound.

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred for 2 hours
  3. washthe organic layer is washed two times with H2O
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced vacuum
  7. customto yield the product
  8. customThis material is purified via silica gel chromatography
  9. washwhile eluting with a suitable eluent, such as hexanes/ethyl acetate

Sources & evidence

ORD record
ord-48723756bd9c4a2fadfe460bfb93205f
Source dataset
uspto-grants-2005_05
Patent number
US06900353B2

Reaction notes

Loading…