Triethylamine → HCID 58869158, compound

HRID 2355229Notes

Reaction equation

HRID 2355229 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][NH:21][CH3:22])[O:17]3)=[CH:12][CH:11]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.BrC[C:32]([O:34][CH3:35])=[O:33]>CN1C(=O)CCC1>[CH3:35][O:34][C:32](=[O:33])[CH2:22][NH:21][CH2:20][C@H:16]1[CH2:15][CH2:14][C:13]2[C:18](=[CH:19][C:10]([S:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)(=[O:9])=[O:8])=[CH:11][CH:12]=2)[O:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 60984Methyl bromoacetateHCID 58869134HCID 58869134, compound

Product 1

HCID 58869158HCID 58869158, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
0 °C

Procedure

(R)-(7-Benzenesulfonyl-chroman-2-ylmethyl)-methyl-amine (81 mg, 2.6 mmol) and triethylamine (0.2 mL) were added to 0.5 mL NMP and the mixture was cooled to 0° C. with stirring. Methyl 2-bromoacetate (26 uL) was added, and the reaction mixture was stirred for two hours at room temperature, 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 40 mg of (R)-[(7-benzenesulfonyl-chroman-2-ylmethyl)-amino]-acetic acid methyl ester.

Workup

  1. stirringthe reaction mixture was stirred for two hours at room temperature
  2. customquenched by addition of water
  3. extractionThe mixture was extracted with methylene chloride
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customPurification of the residue by flash chromatography

Sources & evidence

ORD record
ord-e3f5247f1f6949a79d4f50d3c6657c36
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

Loading…