Water → HCID 86752472, compound

HRID 1600076Notes

Reaction equation

HRID 1600076 reaction equation
Cl.[C:2]([C@H:5]1[CH2:10][CH2:9][C@H:8]([CH2:11][NH:12][C:13](=[O:33])[C@@H:14]2[CH2:18][CH2:17][CH2:16][N:15]2[C:19](=[O:32])[C@H:20](NC(OCC)=O)[CH2:21][C:22](C)(C)[CH3:23])[CH2:7][CH2:6]1)(=[NH:4])[NH2:3].[C:34](=[O:37])([O-])[O-:35].[Na+].[Na+].Cl.ON.[OH2:43]>C(O)C>[C:8]([O:35][C:34]([NH:3][CH:2]1[CH2:5][CH2:6][CH2:23][CH2:22][C@@H:21]1[CH2:20][C:19]([N:15]1[CH2:16][CH2:17][CH2:18][C@H:14]1[C:13]([NH:12][CH2:11][C:8]1[CH:7]=[CH:6][C:5]([C:2](=[N:4][OH:43])[NH2:3])=[CH:10][CH:9]=1)=[O:33])=[O:32])=[O:37])([CH3:11])([CH3:9])[CH3:7]

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 178473529HCID 178473529, compound

Product 1

HCID 86752472HCID 86752472, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the compound (0.94 g, 2 mmol) obtained in the item (c) of Example 1 in ethanol (15 ml), a solution of sodium carbonate (0.17 g, 1.6 mmol) in water (3 ml) and hydroxyamine hydrochloride (0.22 g, 3.2 mmol) are added. After the reaction mixture is heated at reflux for 8 hours, thesolvent is evaporated and the resulting residue is purified with silica gelcolumn chromatography (chloroform-methanol) to give 0.84 g of the titled compound (84%).

Workup

  1. temperatureAfter the reaction mixture is heated
  2. temperatureat reflux for 8 hours
  3. customthesolvent is evaporated
  4. customthe resulting residue is purified with silica gelcolumn chromatography (chloroform-methanol)

Sources & evidence

ORD record
ord-003dfc78760947179ddeb589eb7dc8e4
Source dataset
uspto-grants-1998_04
Patent number
US05744487

Reaction notes

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