Methanol → HCID 59472976, compound

HRID 1678784Notes

Reaction equation

HRID 1678784 reaction equation
[NH:1]([C:3]1[N:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[C:6]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:7]([C:13]1[CH:27]=[CH:26][C:16]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:15][CH:14]=1)=[N:8]2)[NH2:2].CO.[C:36](OC)(OC)(OC)[CH3:37].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:36][C:37]1[N:12]2[C:3]([C:4]3[CH:5]=[C:6]([C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=4)[C:7]([C:13]4[CH:14]=[CH:15][C:16]([CH2:17][NH:18][C:19](=[O:25])[O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:26][CH:27]=4)=[N:8][C:9]=3[CH:10]=[CH:11]2)=[N:1][N:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 15050Trimethyl orthoacetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 59472955HCID 59472955, compound

Product 1

HCID 59472976HCID 59472976, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of 16-2 (5 g, 11.3 mMol) in 20 mL of 3:1 toluene:methanol was added trimethyl orthoacetate (1.8 g, 15.3 mMol) and p-toluenesulfonic acid monohydrate (0.1 g, 0.6 mMol). The reaction was heated to 100° C. in a microwave reactor for 35 minutes. After cooling to room temperature, the solvent was removed under reduced pressure. The residue was purified using normal phase flash chromatography to yield 17-1 as a solid. LC/MS (M+1) calculated: 466.6 observed: 466.2

Workup

  1. temperatureAfter cooling to room temperature
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was purified

Sources & evidence

ORD record
ord-d730916fbeac4586b21f2e84e0ad3423
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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