Methanol → HCID 77750311, compound

HRID 1069032Notes

Reaction equation

HRID 1069032 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]([CH:38]1[CH2:40][CH:39]1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:13]1[C:14]2[N:25]=[N:24][N:23]([CH:26]3[CH:30]4[O:31]C(C)(C)[O:33][CH:29]4[CH:28]([CH2:36][OH:37])[CH2:27]3)[C:15]=2[N:16]=[C:17]([S:19][CH2:20][CH2:21][CH3:22])[N:18]=1.CO.C(OCC)(=O)C>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH2:11][N:12]([CH:38]1[CH2:40][CH:39]1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[C:13]1[C:14]2[N:25]=[N:24][N:23]([CH:26]3[CH2:27][CH:28]([CH2:36][OH:37])[CH:29]([OH:33])[CH:30]3[OH:31])[C:15]=2[N:16]=[C:17]([S:19][CH2:20][CH2:21][CH3:22])[N:18]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 8857Ethyl AcetateHCID 86757049HCID 86757049, compound

Product 1

HCID 77750311HCID 77750311, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of the product from Example 36, step (a) (1.39 g) in trifluoroacetic acid (1.5 ml)/methanol (15 ml) was stirred for two days. Ethyl acetate was added and the mixture was concentrated. Sodium hydrogen carbonate solution was added and the mixture was extracted with ethyl acetate. The organic extracts were dried, concentrated and purified (SiO2, petrol:acetone 1:1 as eluant) to give the subtitle compound (1.11 g).

Workup

  1. concentrationthe mixture was concentrated
  2. additionSodium hydrogen carbonate solution was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. customThe organic extracts were dried
  5. concentrationconcentrated
  6. custompurified (SiO2, petrol:acetone 1:1 as eluant)

Sources & evidence

ORD record
ord-591f684cdd5d458092d28a7d8843f939
Source dataset
uspto-grants-2001_06
Patent number
US06251910B1

Reaction notes

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