Water → HCID 9881077, compound

HRID 1297135Notes

Reaction equation

HRID 1297135 reaction equation
[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[CH:5][C:6]2[NH:12][C:11](=[O:13])[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1.[H-].[Na+].C1(=O)O[CH2:28][CH2:27][O:26]1.O>CN(C=O)C>[CH3:1][O:2][C:3]1[C:4]([O:21][CH3:22])=[CH:5][C:6]2[N:12]([CH2:28][CH2:27][OH:26])[C:11](=[O:13])[CH2:10][N:9]=[C:8]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:7]=2[CH:20]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7303Ethylene carbonateHCID 24758Sodium hydrideHCID 9965973HCID 9965973, compound

Product 1

HCID 9881077HCID 9881077, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 150 mg (0.50 mmol) of 7,8-dimethoxy-5-phenyl-1,3-dihydro-1,4-benzodiazepin-2-one XXIIaa in 5 ml of DMF, add at 0° C. under an inert atmosphere 21 mg (0.52 mmol) of 60% NaH in oil. Stir at room temperature for 1 hour. Add at 0° C., 53 mg (0.60 mmol) of ethylene carbonate. Stir at room temperature overnight. Add 50 ml of H2O and extract three times with 50 ml of AcOEt; dry on MgSO4, evaporate the AcOEt and purify by silica chromatography (AcOEt 3/hexane 1, then AcOEt). Recrystallize in CHCl3/cHexane. Yield: 40%. M: 128–130° C. 1H-NMR (DMSO, 300 MHz): d 3.36–3.52 (m, 2H, HOCH2), 3.60 (s, 3H, OCH3), 3.70–3.86 (m, 5H, NCH2+OCH3), 4.11 (AB system, ? d=0.77, JAB=9.96, 2H, CH2), 4.77 (m, 1H, OH), 6.60 (s, 1H Ar), 7.39 (s, 1H Ar), 7.42–7.58 (m, 4H Ar). Mass: (M+H)+=341.16.

Workup

  1. additionAdd at 0° C.
  2. stirringStir at room temperature overnight
  3. extractionextract three times with 50 ml of AcOEt
  4. customdry on MgSO4
  5. customevaporate the AcOEt
  6. custompurify by silica chromatography (AcOEt 3/hexane 1
  7. customRecrystallize in CHCl3/cHexane
  8. custom128–130° C

Sources & evidence

ORD record
ord-7f864b9e6185435792c3346fbe2b332d
Source dataset
uspto-grants-2007_07
Patent number
US07250410B2

Reaction notes

Loading…