Hydrochloric Acid → (S)-6-(4-benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acid

HRID 449758Notes

Reaction equation

HRID 449758 reaction equation
[OH-].[K+].C[O:4][C:5](=[O:41])[C@@H:6]([N:28]1[C:40]2[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=2[C:34]2[C:29]1=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH2:7][CH2:8][CH2:9][CH2:10][NH:11][C:12](=[O:27])[C:13]1[CH:18]=[CH:17][C:16]([C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:15][CH:14]=1.C1(C)C=CC=CC=1.Cl>CO>[C:19]([C:16]1[CH:15]=[CH:14][C:13]([C:12]([NH:11][CH2:10][CH2:9][CH2:8][CH2:7][C@H:6]([N:28]2[C:40]3[CH:39]=[CH:38][CH:37]=[CH:36][C:35]=3[C:34]3[C:29]2=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:5]([OH:41])=[O:4])=[O:27])=[CH:18][CH:17]=1)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1140TolueneHCID 14797Potassium HydroxideHCID 58554758(S)-6-(4-Benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester

Product 1

HCID 58554744(S)-6-(4-benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acidYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methanolic KOH (0.050 g, 0.88 mmol) was added to a stirred solution of 6-(4-benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 6 (0.230 g, 0.44 mmol) in a mixture (1:2) of toluene (2 mL) and methanol (4 mL). The resulting reaction mixture was refluxed for 3 h. Subsequently, it was neutralized to pH 3-4 with dil. HCl and extracted with EtOAc (20 mL×2). The combined organic extract was washed with water (15 mL×2) and dried over anhydrous Na2SO4. Removal of solvent under reduced pressure provided 6-(4-benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acid 7 (0.210 g, 98%) as a white solid.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas refluxed for 3 h
  3. extractionextracted with EtOAc (20 mL×2)
  4. extractionThe combined organic extract
  5. washwas washed with water (15 mL×2)
  6. dry with materialdried over anhydrous Na2SO4
  7. customRemoval of solvent under reduced pressure

Sources & evidence

ORD record
ord-d4510e99fe2c49219de79c5a0f09feb9
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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