Hydrochloric Acid → HCID 69781962, compound

HRID 2304238Notes

Reaction equation

HRID 2304238 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11]([Cl:14])(=[O:13])=[O:12].Cl.Cl.[CH3:17][O:18][C:19](=[O:34])[CH:20]([NH2:33])[CH2:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28]([NH2:32])=[N:27][CH:26]=[CH:25]2.[OH-].[Na+].Cl>ClCCl.C(N(CC)CC)C.C(O)(C)(C)C.O.ClCCl.CO.O.O1CCOCC1>[ClH:14].[CH3:17][O:18][C:19](=[O:34])[CH:20]([NH:33][S:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)(=[O:13])=[O:12])[CH2:21][C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[C:28]([NH2:32])=[N:27][CH:26]=[CH:25]2

Participants

11

Reactant 4

HCID 313Hydrochloric AcidHCID 71252-Naphthalenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 69780590HCID 69780590, compound

Product 1

HCID 69781962HCID 69781962, compoundYield 35.8%

Reagents, catalysts & solvents 6

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolventHCID 312751,4-DioxaneSolventHCID 21226129Dichloromethane methanolSolventHCID 714019492-Methylpropan-2-ol--water (1/1)Solvent

Procedure

0.10 g of 2-naphthalenylsulfonylchloride dissolved in 0.8 mL of dichloromethane and 0.2 mL of dioxane was added to a solution of 0.13 g of 1j in 6 mL dichloromethane and 0.17 mL of triethylamine at 0° C. After stirring at room temperature for 1 hour water was added, sodium hydroxide was added until pH 8-9 and the mixture was extracted with dichloromethane. The dichloromethane extract was dried (MgSO4) and concentrated. Purification (silica gel, dichloromethane/methanol 95/5), addition of one equivalent of hydrochloric acid and lyophilisation (t-butanol/water) gave 69 mg of 11a. 1H-NMR 200 MHz (CDCl3) δ: 3.00-3.34 (2H, m), 3.49 (3H, s), 4.34 (1H, dd, J=5 Hz and J=9 Hz), 6.72 (1H, d, J=7 Hz), 7.25-7.87 (9H, m), 8.04 (1H, d, J=8 Hz), 8.16 (1H, d, J=2 Hz).

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with dichloromethane
  3. extractionThe dichloromethane extract
  4. dry with materialwas dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1a9624eb005348c0aeca0beb1c71adbc
Source dataset
uspto-grants-2002_08
Patent number
US06432955B1

Reaction notes

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