Hydrochloric Acid → HCID 21968720, compound

HRID 1387447Notes

Reaction equation

HRID 1387447 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 mmol) 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-c7a50727011a4ef692ba384238b25184
Source dataset
uspto-grants-2001_07
Patent number
US06268378B1

Reaction notes

Loading…