Methanol → HCID 58158127, compound

HRID 1916278Notes

Reaction equation

HRID 1916278 reaction equation
[NH2:1][C:2]1[C:7]([C:8]([NH2:10])=[O:9])=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:13][CH:12]=2)[C:5]([C:21]#[N:22])=[C:4]([S:23][CH2:24][C:25]2[N:26]=[C:27]([C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[S:28][CH:29]=2)[N:3]=1.O.[C:38]1(C)C=CC(S(O)(=O)=O)=C[CH:39]=1.CO>C(=O)C>[Cl:36][C:33]1[CH:32]=[CH:31][C:30]([C:27]2[S:28][CH:29]=[C:25]([CH2:24][S:23][C:4]3[C:5]([C:21]#[N:22])=[C:6]([C:11]4[CH:12]=[CH:13][C:14]([O:17][CH2:18][CH2:19][OH:20])=[CH:15][CH:16]=4)[C:7]4[C:8](=[O:9])[NH:10][CH:38]([CH3:39])[NH:1][C:2]=4[N:3]=3)[N:26]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 521998p-Toluenesulfonic acid monohydrateHCID 58158129HCID 58158129, compound

Product 1

HCID 58158127HCID 58158127, compound

Reagents, catalysts & solvents 1

HCID 177AcetaldehydeSolvent

Procedure

Under argon, 138 mg (0.256 mmol) of the compound from Example 22A were initially charged in 3 ml of acetaldehyde, a spatula tip of 4-toluenesulfonic acid monohydrate was added and the mixture was stirred at RT for 1 h. 2.5 ml of methanol were then added to the reaction solution, and after 2 h the mixture was concentrated and the residue was purified by column chromatography (silica gel, toluene/acetonitrile 2:1→1:1).

Workup

  1. concentrationafter 2 h the mixture was concentrated
  2. customthe residue was purified by column chromatography (silica gel, toluene/acetonitrile 2:1→1:1)

Sources & evidence

ORD record
ord-8255ee4025794634a76bf30316d12626
Source dataset
uspto-grants-2013_12
Patent number
US08618119B2

Reaction notes

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