Acetic Acid → HCID 19876845, compound

HRID 1886095Notes

Reaction equation

HRID 1886095 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:22]=[C:21]4[C:17]([CH2:18][CH:19]([CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[C:38]([OH:40])=[O:39])[CH:20]4[S:23][CH2:24][CH2:25][CH2:26][C:27]([O:29]C)=[O:28])=[CH:16][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-].CC(O)=O>C1COCC1.CO>[Cl:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8]([CH2:12][O:13][C:14]3[CH:22]=[C:21]4[C:17]([CH2:18][CH:19]([CH2:31][C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=5[C:38]([OH:40])=[O:39])[CH:20]4[S:23][CH2:24][CH2:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:16][CH:15]=3)=[N:9]2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 19876837HCID 19876837, compound

Product 1

HCID 19876845HCID 19876845, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of the product of Step 6 (131 mg, 0.229 mmol) in THF/MeOH (1.5 ml, 1:2) was added 1M K2CO3 (0.687 ml). The mixture was stirred at room temperature for 20 hrs. NH4Cl solution was added and the pH was adjusted to 5 with HOAc. Extraction with EtOAc followed by chromatography of the crude product on silicic acid (eluted with 30% EtOAc/hexane) gave 100 mg of the title compounds.

Workup

  1. extractionExtraction with EtOAc

Sources & evidence

ORD record
ord-a0e43f6293554089af2d69e5b57a8875
Source dataset
uspto-grants-1992_09
Patent number
US05149703

Reaction notes

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