4-{[(benzyloxy)carbonyl]amino}benzoic acid → HCID 58554730, compound

HRID 449767Notes

Reaction equation

HRID 449767 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN=C=NCCCN(C)C.Cl.[CH:33]1[C:45]2[N:44]([C@@H:46]([CH2:57][CH2:58][C:59]([O:61][CH2:62][CH2:63]O)=[O:60])[C:47]([O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:48])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH:33]1[C:45]2[N:44]([C@@H:46]([CH2:57][CH2:58][C:59]([O:61][CH2:62][CH2:63][O:17][C:16](=[O:18])[C:15]3[CH:14]=[CH:13][C:12]([NH:11][C:9]([O:8][CH2:1][C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=4)=[O:10])=[CH:20][CH:19]=3)=[O:60])[C:47]([O:49][CH2:50][C:51]3[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=3)=[O:48])[C:43]3[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:37]=2[CH:36]=[CH:35][CH:34]=1

Participants

6

Reactant 3

HCID 2201714-{[(benzyloxy)carbonyl]amino}benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 58554741HCID 58554741, compound

Product 1

HCID 58554730HCID 58554730, compoundYield 63.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(benzoyloxycarbonylamino)benzoic acid 10 (0.650 g, 2.40 mmol), EDC HCl (0.510 g, 2.65 mmol) and DMAP (0.044 g, 0.36 mmol) in CH2Cl2 (20 mL) was added (S)-1-benzyl 5-(2-hydroxyethyl) 2-(9H-carbazol-9-yl)pentanedioate 23 (0.800 g, 1.85 mmol). After the reaction mixture was refluxed for 6 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 silica gel column chromatography using CH3OH:CH2Cl2 (1:99) as eluent to afford (S)-1-benzyl 5-(2-(4-(benzyloxycarbonylamino)benzoyloxy)-ethyl) 2-(9H-carbazol-9-yl)pentanedioate 24 (0.80 g, 63%) as a white solid.

Workup

  1. temperatureAfter the reaction mixture was refluxed for 6 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 silica gel column chromatography

Sources & evidence

ORD record
ord-580205fcf28b4b2ab9fc181fc0827e6a
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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