Methanol → HCID 58392549, compound

HRID 561573Notes

Reaction equation

HRID 561573 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:15]3[C:23]4[C:18](=[C:19]([CH2:24][S:25][CH3:26])[CH:20]=[CH:21][CH:22]=4)[NH:17][CH:16]=3)[CH2:11][CH2:12][C:13]#[N:14])=[CH:9][C:4]=2[CH:3]=[CH:2]1.ClCCl.ClC1C=CC=C(C(OO)=[O:38])C=1.CO>C(OCC)(=O)C>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:15]3[C:23]4[C:18](=[C:19]([CH2:24][S:25]([CH3:26])=[O:38])[CH:20]=[CH:21][CH:22]=4)[NH:17][CH:16]=3)[CH2:11][CH2:12][C:13]#[N:14])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 70297m-Chloroperbenzoic acidHCID 58392495HCID 58392495, compound

Product 1

HCID 58392549HCID 58392549, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

157 mg (0.42 mmol) of the compound from Example 52 were introduced into 28 ml of dichloromethane at 0° C., 102 mg (0.42 mmol) of 70% pure meta-chloroperbenzoic acid were added, and the mixture was stirred at RT for 2 h. 2 ml of methanol and a little ethyl acetate were added, and the mixture was extracted with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The phases were separated, and the solvents were removed from the organic phase in vacuo. The crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient) and afforded 141 mg (86% of theory) of the title compound as mixture of diastereomers.

Workup

  1. extractionthe mixture was extracted with water, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. customThe phases were separated
  3. customthe solvents were removed from the organic phase in vacuo
  4. customThe crude product was purified by preparative HPLC (mobile phase: acetonitrile/water gradient)

Sources & evidence

ORD record
ord-a2c3c10f3e324fb890070fb36c0d167b
Source dataset
uspto-grants-2011_11
Patent number
US08063234B2

Reaction notes

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