HCID 58869132, compound → HCID 58869174, compound

HRID 2355206Notes

Reaction equation

HRID 2355206 reaction equation
[C:1]([O:5][C:6](=[O:30])[N:7]([CH2:9][CH:10]1[CH2:19][C:18](=O)[C:17]2[C:12](=[CH:13][C:14]([S:21](C3C=CC=CC=3)(=[O:23])=[O:22])=[CH:15][CH:16]=2)[O:11]1)[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Li][C:32]([CH3:35])([CH3:34])C>C1COCC1>[C:34]1([S:21]([C:14]2[C:13]([C:6]([OH:30])=[O:5])=[C:12]3[C:17]([CH2:18][CH2:19][CH:10]([CH2:9][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:30])[CH3:8])[O:11]3)=[CH:16][CH:15]=2)(=[O:22])=[O:23])[CH:32]=[CH:35][CH:3]=[CH:1][CH:2]=1

Participants

4

Reactant 2

HCID 58869132HCID 58869132, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 58869174HCID 58869174, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (7-benzenesulfonyl-4-oxo-chroman-2-ylmethyl)-methyl-carbamic acid tert-butyl ester (141 mg, 0.338 mmol) in THF (15 mL) cooled at −78° C. was added t-BuLi (1.7M in hexanes, 0.68 mL) dropwise. The reaction was allowed to warm to 0° C. for 3 hours, then it was quenched with CO2 (gas) and diluted with water. The volatiles were removed in vacuo and the aqueous residue was washed with Et2O and then acidified to give a white precipitate that was filtered and dried to afford 7-benzenesulfonyl-2-[(tert-butoxycarbonyl-methyl-amino)-methyl]-chroman-8-carboxylic acid (55 mg, 35% yield) as a white powder.

Workup

  1. customit was quenched with CO2 (gas)
  2. additiondiluted with water
  3. customThe volatiles were removed in vacuo
  4. washthe aqueous residue was washed with Et2O
  5. customto give a white precipitate that
  6. filtrationwas filtered
  7. customdried

Sources & evidence

ORD record
ord-a8f93219108b496688b18e727d86cc07
Source dataset
uspto-grants-2010_07
Patent number
US07754759B2

Reaction notes

Loading…