Water → HCID 67076794, compound

HRID 2094736Notes

Reaction equation

HRID 2094736 reaction equation
C[O:2][C:3]([C:5]1([NH:14][C:15](=[O:36])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33][CH2:34][NH2:35])[CH:28]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].O.[C:38](OC(=O)C)(=[O:40])[CH3:39]>>[C:38]([NH:35][CH2:34][CH2:33][C:29]1[CH:28]=[C:27]([CH2:26][CH2:25][O:24][C:18]2[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=2[O:22][CH3:23])[C:15]([NH:14][C:5]2([C:3]([OH:2])=[O:4])[CH2:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH2:6]2)=[O:36])[CH:32]=[CH:31][CH:30]=1)(=[O:40])[CH3:39]

Participants

4

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 67076803HCID 67076803, compound

Product 1

HCID 67076794HCID 67076794, compound

Procedure

The compound of Step 2 of example 246 (85 mg, 0.174 mmol) was dissolved in acetic anhydride and stirred under reflux for 30 min. Water was added in excess and the mixture was refluxed for 10 min. After cooling, the mixture was extracted with EA, the combined extracts were dried over sodium sulfate and evaporated to dryness. The residue was purified by RP HPLC (water/ACN gradient) to yield the methyl ester of the title compound. Hydrolysis of this ester in analogy to example 2 yielded 17 mg of the title compound.

Workup

  1. temperatureunder reflux for 30 min
  2. temperaturewas refluxed for 10 min
  3. temperatureAfter cooling
  4. extractionthe mixture was extracted with EA
  5. dry with materialthe combined extracts were dried over sodium sulfate
  6. customevaporated to dryness
  7. customThe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-0971bdd9ed1945ce9765bf3d00084d8c
Source dataset
uspto-grants-2013_05
Patent number
US08445530B2

Reaction notes

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