(2R)-2-(Acetyloxy)propanoyl chloride → (r)-Acetic acid 1-[(7-benzenesulfonyl-chroman-2-ylmethyl)-carbamoyl]-ethyl ester

HRID 2355231Notes

Reaction equation

HRID 2355231 reaction equation
[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C@H:16]([CH2:20][NH2:21])[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:23]([C@H:25]([O:27][C:28](=[O:30])[CH3:29])[CH3:26])=[O:24]>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][CH:16]([CH2:20][NH:21][C:23]([C@H:25]([O:27][C:28](=[O:30])[CH3:29])[CH3:26])=[O:24])[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15557611(2R)-2-(Acetyloxy)propanoyl chlorideHCID 58869146(R)-C-(7-Benzenesulfonyl-chroman-2-yl)-methylamine

Product 1

HCID 131728243(r)-Acetic acid 1-[(7-benzenesulfonyl-chroman-2-ylmethyl)-carbamoyl]-ethyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)—C-(7-Benzenesulfonyl-chroman-2-yl)-methylamine (57 mg, 0.19 mmol) triethylamine (0.02 mL) and acetic acid 1-(R)-chlorocarbonyl-ethyl ester were added to 1 mL methylene chloride, and the mixture was stirred for two hours at room temperature. The reaction was quenched by addition of water, and the mixture was extracted with methylene chloride. The combined organic layers were washed with water and brine, dried (Na2SO4), filtered and contrated under reduced pressure. Purification of the residue by flash chromatography gave 7.59 mg of (R)-acetic acid 1-[(7-benzenesulfonyl-chroman-2-ylmethyl)-carbamoyl]-ethyl ester.

Workup

  1. customThe reaction was quenched by addition of water
  2. extractionthe mixture was extracted with methylene chloride
  3. washThe combined organic layers were washed with water and brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-72aea6534f9f4bbfb0aeac34df25a8fa
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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