Dichloromethane → HCID 69732176, compound

HRID 967783Notes

Reaction equation

HRID 967783 reaction equation
Cl.C(N=C=NCCCN(C)C)C.ClCCl.C(C1C=C(CC[N:26]2[CH2:31][CH2:30][C:29]([CH2:33][N:34]([CH3:45])[C:35]3[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=3)([OH:32])[CH2:28][CH2:27]2)C=CC=1)#N.[CH3:46][S:47]([C:50]1[CH:55]=[CH:54][C:53]([CH2:56][C:57]([OH:59])=O)=[CH:52][CH:51]=1)(=[O:49])=[O:48]>O>[OH:32][C:29]1([CH2:33][N:34]([CH3:45])[C:35]2[CH:44]=[CH:43][C:38]([C:39]([O:41][CH3:42])=[O:40])=[CH:37][CH:36]=2)[CH2:30][CH2:31][N:26]([C:57](=[O:59])[CH2:56][C:53]2[CH:52]=[CH:51][C:50]([S:47]([CH3:46])(=[O:48])=[O:49])=[CH:55][CH:54]=2)[CH2:27][CH2:28]1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 5723454-Mesylphenylacetic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22930205HCID 22930205, compound

Product 1

HCID 69732176HCID 69732176, compoundYield 129.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.68 g) was added to a dichloromethane solution (15 mL) of the compound (0.90 g) obtained in Step 3 of Example 25 and 4-methylsulfonylphenylacetic acid (0.76 g) and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into cold water (80 mL) and then separated, and the aqueous layer was extracted with dichloromethane. The organic layer was combined and washed with water and brine successively, and then dried over anhydrous sodium sulfate. After the solvent was removed under reduce pressure, the residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=8:1) to obtain the titled compound (1.36 g) as crystals.

Workup

  1. customseparated
  2. extractionthe aqueous layer was extracted with dichloromethane
  3. washwashed with water and brine successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAfter the solvent was removed
  6. customthe residue was purified by silica gel column chromatography (eluent; dichloromethane:methanol=8:1)

Sources & evidence

ORD record
ord-56a58797f00d4fff9aeb0c95da310b93
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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