Dichloromethane → HCID 86679428, compound

HRID 1776471Notes

Reaction equation

HRID 1776471 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:5][C:4]=1[NH:19][S:20]([CH3:23])(=[O:22])=[O:21].Cl.Cl[CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1.[H-].[Na+].C(Cl)Cl>CN(C=O)C.C(Cl)Cl.CCOC(C)=O>[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]([CH3:16])[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:12])[CH3:13])=[CH:5][C:4]=1[N:19]([CH2:26][CH2:27][N:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1)[S:20]([CH3:23])(=[O:22])=[O:21]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 24758Sodium hydrideHCID 77210Morpholine, 4-(2-chloroethyl)-, hydrochloride (1:1)HCID 86679426HCID 86679426, compound

Product 1

HCID 86679428HCID 86679428, compoundYield 45.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 21226138Dichloromethane ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

tert-Butyl 4-methoxy-3-(methylsulfonamido)benzyl(methyl)carbamate (189.1 mg, 0.549 mmol) was dissolved in dry DMF (10 ml) and cooled to 0° C. Nan (60% w/w dispersion in mineral oil, 48.3 mg, 1.208 mmol) was added, and the mixture was stirred 5 minutes at 0° C. and then 5 minutes at RT. 4-(2-Chloroethyl)morpholine hydrochloride (123 mg, 0.659 mmol) was added, and the mixture was stirred at RT for overnight. Additional NaH (43.93 mg, 1.098 mmol) was added over 4 days with stirring at RT. The reaction was quenched with water and brine and extracted with Et2O and twice with EtOAc. The combined organic layers were dried over Na2SO4, and the solvent was evaporated under vacuum. The crude product was purified by silica gel cartridge using as eluent:DCM to DCM/EtOAc 2:8 to give tert-butyl 4-methoxy-3-(N-(2-morpholinoethyl)methylsulfonamido)benzyl(methyl)carbamate (114 mg, 0.249 mmol, 45.4% yield).

Workup

  1. additionNan (60% w/w dispersion in mineral oil, 48.3 mg, 1.208 mmol) was added
  2. custom5 minutes
  3. customat RT
  4. stirringthe mixture was stirred at RT for overnight
  5. stirringwith stirring at RT
  6. customThe reaction was quenched with water and brine
  7. extractionextracted with Et2O and twice with EtOAc
  8. dry with materialThe combined organic layers were dried over Na2SO4
  9. customthe solvent was evaporated under vacuum
  10. customThe crude product was purified by silica gel cartridge

Sources & evidence

ORD record
ord-ee63c528eb6e43c5aff9671225722eed
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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