Hydrochloric Acid → HCID 21968720, compound

HRID 1108398Notes

Reaction equation

HRID 1108398 reaction equation
Cl.C([O:9][C:10](=[O:39])[C@@H:11]([NH:31]C(OC(C)(C)C)=O)[CH2:12][C:13]1[O:17][N:16]=[C:15]([CH2:18][CH2:19][CH2:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[N:24][CH:25]=[CH:26][CH:27]=3)[N:22]=2)[N:14]=1)C1C=CC=CC=1.CN1CCOCC1.[C:47]1([S:53](Cl)(=[O:55])=[O:54])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1.[OH-].[Na+]>O1CCOCC1.C(OCC)(=O)C.C(O)C.ClCCl>[C:47]1([S:53]([NH:31][C@@H:11]([CH2:12][C:13]2[O:17][N:16]=[C:15]([CH2:18][CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[N:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[N:14]=2)[C:10]([OH:9])=[O:39])(=[O:55])=[O:54])[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1

Participants

10

Reactant 5

HCID 313Hydrochloric AcidHCID 7369Benzenesulfonyl chlorideHCID 79724-MethylmorpholineHCID 14798Sodium HydroxideHCID 53726559HCID 53726559, compound

Product 1

HCID 21968720HCID 21968720, compound

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 4M HCl in dioxane (20 mL) was added to 8-5 (0.7 g, 1.4 mmol). After 30 minutes, the solvent was evaporated to give a white solid. To this solid (0.3 g, 0.64 mol) was added dichloromethane (10 mL), and NMM (0.7 mL, 6.4 mmol), and the mixture was cooled to 0° C. Phenylsulfonyl chloride (0.081 mL, 0.64 mmol) was added. After 30 minutes, the mixture was diluted with ethyl acetate, washed with sat. NaHCO3, brine, and dried over MgSO4. Evaporation gave the crude ester 8-6, which was dissolved in ethanol (5 mL); sodium hydroxide (0.7 mL, 1 N in water) was added. After 1 hr, the solvent was evaporated, and the residue was chromatographed (silica gel, 25:10:1:1 followed by 15:10:1:1 ethyl acetate /EtOH /water NH4OH) to give 8-7 as a white solid.

Workup

  1. customthe solvent was evaporated
  2. customto give a white solid
  3. waitAfter 30 minutes
  4. washwashed with sat. NaHCO3, brine
  5. dry with materialdried over MgSO4
  6. customEvaporation
  7. customgave the crude ester 8-6, which
  8. waitAfter 1 hr
  9. customthe solvent was evaporated
  10. customthe residue was chromatographed (silica gel, 25:10:1:1 followed by 15:10:1:1 ethyl acetate /EtOH /water NH4OH)

Sources & evidence

ORD record
ord-efa32e8bb0db4902b56a406a4fb7c7ef
Source dataset
uspto-grants-2000_05
Patent number
US06066648

Reaction notes

Loading…