Dichloromethane → HCID 66727251, compound

HRID 1845958Notes

Reaction equation

HRID 1845958 reaction equation
[CH2:1](N(CC)CC)C.ClCCl.C(OC(NC(C)(C)CN(C(OC(C)(C)C)=O)CCCO)=O)C1C=CC=CC=1.[C:38]([O:42][C:43]([N:45]([CH2:63][CH2:64][CH2:65][OH:66])[CH2:46][C@@H:47]([NH:49][S:50]([C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][CH:62]=1)[CH:59]=[N:58][CH:57]=[CH:56]2)(=[O:52])=[O:51])[CH3:48])=[O:44])([CH3:41])([CH3:40])[CH3:39]>O>[C:38]([O:42][C:43]([N:45]([CH2:63][CH2:64][CH2:65][OH:66])[CH2:46][C:47]([NH:49][S:50]([C:53]1[CH:54]=[C:55]2[C:60](=[CH:61][CH:62]=1)[CH:59]=[N:58][CH:57]=[CH:56]2)(=[O:52])=[O:51])([CH3:1])[CH3:48])=[O:44])([CH3:41])([CH3:40])[CH3:39]

Participants

6

Reactant 4

HCID 6344Dichloromethane2×HCID 8471TriethylamineHCID 58080792HCID 58080792, compound2×HCID 66727253HCID 66727253, compound2×

Product 1

HCID 66727251HCID 66727251, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.7 mL of triethylamine was added to a dichloromethane (20 mL) solution of 550 mg of 2-(benzyloxycarbonylamino)-1-(tert-butoxycarbonyl-3-hydroxypropylamino)-2-methylpropane (Reference Compound 37). To this reaction solution, a dichloromethane solution (100 mL) of 6-chlorosulfonylisoquinoline (Reference Compound 2) synthesized according to Reference Example 2 was added, and the mixture was stirred at room temperature for 16 hours. After the completion of reaction, water was added, followed by extraction with dichloromethane (20 mL×3). The extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel chromatography (acetone:hexane=1:1) to obtain 140 mg of the compound of interest as a brown oil (14%).

Workup

  1. additionwas added
  2. additionwas added
  3. extractionfollowed by extraction with dichloromethane (20 mL×3)
  4. dry with materialThe extract was dried over anhydrous sodium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated
  7. customthe obtained crude product
  8. customwas purified by silica gel chromatography (acetone:hexane=1:1)

Sources & evidence

ORD record
ord-8432d9ce78dc453793ae0118bf367c19
Source dataset
uspto-grants-2015_02
Patent number
US08951997B2

Reaction notes

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