4-{[(benzyloxy)carbonyl]amino}benzoic acid → HCID 67993122, compound

HRID 449763Notes

Reaction equation

HRID 449763 reaction equation
[CH:1]1[C:13]2[N:12]([C@@H:14]([CH2:25][C:26]([O:28][CH2:29][CH2:30][OH:31])=[O:27])[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH2:32]([O:39][C:40]([NH:42][C:43]1[CH:51]=[CH:50][C:46]([C:47](O)=[O:48])=[CH:45][CH:44]=1)=[O:41])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:1]1[C:13]2[N:12]([C@@H:14]([CH2:25][C:26]([O:28][CH2:29][CH2:30][O:31][C:47](=[O:48])[C:46]3[CH:45]=[CH:44][C:43]([NH:42][C:40]([O:39][CH2:32][C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[O:41])=[CH:51][CH:50]=3)=[O:27])[C:15]([O:17][CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 2201714-{[(benzyloxy)carbonyl]amino}benzoic acidHCID 58554765HCID 58554765, compound

Product 1

HCID 67993122HCID 67993122, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

(S)-1-benzyl 4-(2-hydroxyethyl) 2-(9H-carbazol-9-yl)succinate 17 (0.500 g, 1.20 mmol) was added to a solution of 4-(benzoyloxycarbonylamino)benzoic acid 10 (0.389 g, 1.44 mmol), EDCHCl (0.304 g, 1.58 mmol) and DMAP (0.043 g, 0.35 mmol) in CH2Cl2 (10 mL). After the reaction mixture was refluxed for 24 h, the solution was extracted with CH2Cl2 (100 mL) and water (100 mL). The organic layer was washed with brine (100 mL), dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column using CH3OH:CH2Cl2 (1:99) to afford (S)-1-benzyl 4-(2-(4-(benzyloxycarbonylamino)benzoyloxy)ethyl) 2-(9H-carbazol-9-yl)succinate 18 (0.480 g, 60%) as a white solid.

Workup

  1. temperatureAfter the reaction mixture was refluxed for 24 h
  2. extractionthe solution was extracted with CH2Cl2 (100 mL) and water (100 mL)
  3. washThe organic layer was washed with brine (100 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on a silica gel column

Sources & evidence

ORD record
ord-6ace30650c5d4404b5f744872714999a
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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