3-Amino-2-chlorobenzoic acid → HCID 9917165, compound

HRID 1838087Notes

Reaction equation

HRID 1838087 reaction equation
[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH3:12][C:13]1[CH:44]=[CH:43][CH:42]=[CH:41][C:14]=1[CH2:15][NH:16][C:17]([C@@H:19]1[C:23]([CH3:25])([CH3:24])[S:22][CH2:21][N:20]1[C:26](=[O:40])[C@@H:27]([OH:39])[C@@H:28]([NH2:38])[CH2:29][C:30]1[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=1)=[O:18]>CCOC(C)=O>[CH3:12][C:13]1[CH:44]=[CH:43][CH:42]=[CH:41][C:14]=1[CH2:15][NH:16][C:17]([C@@H:19]1[C:23]([CH3:25])([CH3:24])[S:22][CH2:21][N:20]1[C:26](=[O:40])[C@@H:27]([OH:39])[C@@H:28]([NH:38][C:5](=[O:7])[C:4]1[CH:8]=[CH:9][CH:10]=[C:2]([NH2:1])[C:3]=1[Cl:11])[CH2:29][C:30]1[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=1)=[O:18]

Participants

4

Reactant 2

HCID 4593153-Amino-2-chlorobenzoic acidHCID 69879159HCID 69879159, compound

Product 1

HCID 9917165HCID 9917165, compoundYield 81.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

DPP-Cl(68 μl) and TEA(50 μl) were added to a solution of 3-amino-2-chlorobenzoic acid (56 mg) in EtOAc (2 ml), and the mixture was stirred for one hour. After the addition of the compound obtained in Step 2 of Example 1 (141 mg) and TEA (50 μl), the mixture was stirred overnight. The reaction mixture was washed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl, dried over MgSO4. After filtration and concentration, the residue was purified by silica gel column chromatography (CH2Cl2—MeOH), and reprecipitated from a mixture of CH2Cl2 and n-hexane to obtain the title compound (153 mg, 81%).

Workup

  1. stirringthe mixture was stirred overnight
  2. washThe reaction mixture was washed with 5% Na2CO3 (×2), 1N HCl, and 5% NaCl
  3. dry with materialdried over MgSO4
  4. filtrationAfter filtration and concentration
  5. customthe residue was purified by silica gel column chromatography (CH2Cl2—MeOH)
  6. customreprecipitated from a mixture of CH2Cl2 and n-hexane

Sources & evidence

ORD record
ord-f5d2d4d27daf47ebb57762fface7bfcb
Source dataset
uspto-grants-2004_01
Patent number
US06673772B2

Reaction notes

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