Hydrochloric Acid → HCID 9868203, compound

HRID 2354992Notes

Reaction equation

HRID 2354992 reaction equation
[OH-].[Na+].CO[C:5](=[O:27])[C:6]1[CH:11]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:9]=[C:8]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=2)[CH:7]=1.Cl.[NH2:29][C:30]1[S:31][CH:32]=[C:33]([CH3:35])[N:34]=1.O.ON1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CO.C(Cl)Cl.C(OC(=O)C)C>[CH:13]([O:12][C:10]1[CH:9]=[C:8]([O:16][C:17]2[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:24])=[O:25])=[CH:19][CH:18]=2)[CH:7]=[C:6]([CH:11]=1)[C:5]([NH:29][C:30]1[S:31][CH:32]=[C:33]([CH3:35])[N:34]=1)=[O:27])([CH3:15])[CH3:14]

Participants

10

Reactant 6

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 741432-Amino-4-methylthiazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 59649315HCID 59649315, compound

Product 1

HCID 9868203HCID 9868203, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

After adding 0.28 ml (0.56 mmol) of aqueous 2N sodium hydroxide to a solution of 41.0 mg (0.11 mmol) of the obtained sulfone compound in methanol (1.0 ml), the reaction mixture was stirred overnight. Aqueous 2N hydrochloric acid was added to the reaction mixture, extraction was performed with acetic acid ethyl ester, and the organic layer was washed with brine, dried and concentrated under reduced pressure to obtain a crude carboxyl compound. After adding 5.90 mg (0.51 mol) of 2-amino-4-methylthiazole, 9.30 mg (0.068 mmol) of 1-hydroxybenzotriazole hydrate and 13.0 mg (0.068 mol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride to a solution of 12.0 mg (0.034 mmol) of the obtained carboxyl compound in methylene chloride (0.5 ml), the mixture was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=1:1) to obtain the title compound as a white solid. The analysis data for the compound obtained in Production Example 1 are shown below.

Workup

  1. washthe organic layer was washed with brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customto obtain a crude carboxyl compound
  5. stirringthe mixture was stirred at room temperature overnight
  6. concentrationThe reaction mixture was concentrated under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (hexane:acetic acid ethyl ester=1:1)

Sources & evidence

ORD record
ord-72a61f1ece934487973c342e294030db
Source dataset
uspto-grants-2010_07
Patent number
US07754743B2

Reaction notes

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