Benzyloxyacetyl chloride → (R)-N-(7-benzenesulfonyl-chroman-2-ylmethyl)-2-benzyloxy-acetamide

HRID 2355227Notes

Reaction equation

HRID 2355227 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.[CH2:22]([O:29][CH2:30][C:31](Cl)=[O:32])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[C:1]1([S:7]([C:10]2[CH:19]=[C:18]3[C:13]([CH2:14][CH2:15][C@H:16]([CH2:20][NH:21][C:31](=[O:32])[CH2:30][O:29][CH2:22][C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[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 177085Benzyloxyacetyl chlorideHCID 58869146(R)-C-(7-Benzenesulfonyl-chroman-2-yl)-methylamine

Product 1

HCID 58869170(R)-N-(7-benzenesulfonyl-chroman-2-ylmethyl)-2-benzyloxy-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)—C-(7-Benzenesulfonyl-chroman-2-yl)-methylamine (130 mg, 0.43 mmol) triethylamine (0.3 mL) and benzyloxy acetyl chloride 77 uL) were added to 3 mL methylene chloride at 0° C. The reaction mixture was stirred at room temperature for three hours and then quenched by addition of water. The mixture was extracted with methylene chloride and 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 4.34 mg of (R)—N-(7-benzenesulfonyl-chroman-2-ylmethyl)-2-benzyloxy-acetamide.

Workup

  1. customquenched 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-c8e8d311bc2d4d5fb2525daa686d19ce
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

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