Hydrochloric Acid → HCID 44454980, compound

HRID 1179336Notes

Reaction equation

HRID 1179336 reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:41]=[CH:40][C:14]([CH2:15][NH:16][C:17](=[O:39])[CH2:18][N:19]2[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([O:29]C(C)(C)C)=[O:28])[C:22]3[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=3[C:20]2=[O:38])=[CH:13][CH:12]=1.Cl>C(Cl)Cl.C(O)(=O)C.O.O1CCOCC1>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][NH:16][C:17](=[O:39])[CH2:18][N:19]2[CH2:25][CH2:24][CH:23]([CH2:26][C:27]([OH:29])=[O:28])[C:22]3[CH:34]=[CH:35][CH:36]=[CH:37][C:21]=3[C:20]2=[O:38])=[CH:40][CH:41]=1

Participants

7

Reactant 2

HCID 313Hydrochloric AcidHCID 86591656HCID 86591656, compound

Product 1

HCID 44454980HCID 44454980, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.53 g (10 mmol) of the t-butyl ester from Example I was dissolved in a mixture of 10 ml of CH2Cl2, 5 ml of glacial acetic acid and 0.25 ml of water, and the solution was treated with 7 ml of 4 N HCl in dioxane and stirred at room temperature overnight. Toward the end, the solvent was distilled off in vacuo with addition of toluene and the residue was purified by column chromatography (eluent: CH2Cl2/MeOH/50% strength acetic acid, 45/5/1). After stripping off the solvent and digesting with ether, 0.42 g (84%) of amorphous powder remained; FAB-MS [M−H+]: 498.

Workup

  1. distillationToward the end, the solvent was distilled off in vacuo with addition of toluene
  2. customthe residue was purified by column chromatography (eluent: CH2Cl2/MeOH/50% strength acetic acid, 45/5/1)

Sources & evidence

ORD record
ord-2539c82446e943fbb1f4a97c90eb69c4
Source dataset
uspto-grants-2007_10
Patent number
US07279468B2

Reaction notes

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