Ethanol → HCID 69068806, compound

HRID 1698333Notes

Reaction equation

HRID 1698333 reaction equation
C[O:2][C:3]([C@H:5]1[CH2:10][C@@H:9]([N:11]([CH3:22])[S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[CH2:8][N:7]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:6]1)=[O:4].C(O)C.[Li+].[OH-]>O>[C:26]([O:25][C:23]([N:7]1[CH2:8][C@H:9]([N:11]([CH3:22])[S:12]([C:15]2[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=2)(=[O:14])=[O:13])[CH2:10][C@H:5]([C:3]([OH:4])=[O:2])[CH2:6]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 702EthanolHCID 3939Lithium HydroxideHCID 69067396HCID 69067396, compound

Product 1

HCID 69068806HCID 69068806, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of this ester (160 mg, 0.375 mmol), ethanol (4 ml) and 1N LiOH solution (1.88 ml, 1.88 mmol) is stirred for 14 h at RT. The mixture is diluted with H2O and extracted with methyl tert.-butyl ether. The organic layer is discarded, the aqueous phase acidified to pH 2 with a 10% NaHSO4 solution and extracted three times with methyl tert-butyl ether. The combined organic extracts are dried (Na2SO4) and evaporated to afford the title compound. MS (LC-MS): 413.4 [M+H]+; tR (HPLC, Symmetry C18; 5-100% CH3CN+0.1% TFA/H2O+0.1% TFA for 7 min, flow 1.5 ml/min): 4.31 min.

Workup

  1. extractionextracted with methyl tert.-butyl ether
  2. extractionextracted three times with methyl tert-butyl ether
  3. dry with materialThe combined organic extracts are dried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-2bdcc9fc919f4dc984555a4c22bbeece
Source dataset
uspto-grants-2012_04
Patent number
US08163773B2

Reaction notes

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