Water → HCID 67076794, compound

HRID 521508Notes

Reaction equation

HRID 521508 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-1a7c8035b6d34435b2a83854043bf6d5
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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