Acetic Acid → HCID 59732421, compound

HRID 131563Notes

Reaction equation

HRID 131563 reaction equation
[Cl:1][C:2]1[N:3]([CH2:9][C:10]2[S:25][C:13]3[N:14]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:15](=[O:20])[N:16]([CH3:19])[C:17](=[O:18])[C:12]=3[C:11]=2[C:26]([N:28]2[CH2:32][CH:31]([O:33][Si](C(C)(C)C)(C)C)[CH2:30][O:29]2)=[O:27])[C:4](=[O:8])[S:5][C:6]=1[Cl:7].C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[N:3]([CH2:9][C:10]2[S:25][C:13]3[N:14]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:15](=[O:20])[N:16]([CH3:19])[C:17](=[O:18])[C:12]=3[C:11]=2[C:26]([N:28]2[CH2:32][CH:31]([OH:33])[CH2:30][O:29]2)=[O:27])[C:4](=[O:8])[S:5][C:6]=1[Cl:7]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 68806737HCID 68806737, compound

Product 1

HCID 59732421HCID 59732421, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of the product of step e) (180 mg) in THF (5 ml) under a nitrogen atmosphere, was added glacial acetic acid (0.10 ml) follwed by 1 N tetrabutylammonium fluoride solution in THF (0.5 ml). After 16 h at ambient temperature the mixture was neutralised with sat sodium bicarbonate solution and extracted into ethyl acetate. The organics were washed with water, and dried over magnesium sulphate. Concentration in vacuo gave a white solid that was purified by reverse phase HPLC to give the title compound as a white solid (100 mg). δ 1HDMSO 0.92 (6H,d), 2.18 (1H,non), 3.20 (3H,s), 3.43-4.11 (6H,m), 4.60-4.76 (1H,m), 5.04-5.11 (2H,m), 5.51 (1H,s).

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organics were washed with water
  3. dry with materialdried over magnesium sulphate
  4. concentrationConcentration in vacuo
  5. customgave a white solid
  6. customthat was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-f1a4fd2ee4ce49699db9c357347a43c5
Source dataset
uspto-grants-2008_06
Patent number
US07384950B2

Reaction notes

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