Tetrahydrofuran → HCID 136141600, compound

HRID 2375077Notes

Reaction equation

HRID 2375077 reaction equation
[O:1]=[C:2]1[C:13]2[C:14]3[C:6](=[C:7]([C:27]4[CH:28]=[C:29]([CH:35]=[CH:36][CH:37]=4)[CH2:30][O:31]C(=O)C)[NH:8][C:9]=3[CH:10]=[C:11]([NH:15][C:16]([C@@H:18]3[CH2:20][C@H:19]3[C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[O:17])[CH:12]=2)[CH:5]=[N:4][NH:3]1.C([O-])([O-])=O.[K+].[K+].O1CCCC1>CO>[OH:31][CH2:30][C:29]1[CH:28]=[C:27]([C:7]2[NH:8][C:9]3[CH:10]=[C:11]([NH:15][C:16]([C@@H:18]4[CH2:20][C@H:19]4[C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=4)=[O:17])[CH:12]=[C:13]4[C:2](=[O:1])[NH:3][N:4]=[CH:5][C:6]=2[C:14]=34)[CH:37]=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 136181626HCID 136181626, compound

Product 1

HCID 136141600HCID 136141600, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The title compound of Example 85 (0.288 g, 0.58 mmol) and K2CO3 (0.161 g, 1.17 mmol) were stirred in methanol (0.2 M, 1.7 mL) and tetrahydrofuran (0.2 M, 1.7 mL) for 1.5 hours at 22° C. After the solution was filtered and acidified with two drops of glacial acetic acid, the volatiles were removed in vacuo. Silica gel chromatography (40:60 to 0:100 hexane/ethyl acetate) afforded the title compound (0.26 g) as a yellow powder in 95% yield.

Workup

  1. filtrationAfter the solution was filtered
  2. customthe volatiles were removed in vacuo

Sources & evidence

ORD record
ord-1ce43b0157b34e0fb1b85a6484fa2acb
Source dataset
uspto-grants-2008_12
Patent number
US07462713B2

Reaction notes

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