Hydrochloric Acid → HCID 135975028, compound

HRID 2075753Notes

Reaction equation

HRID 2075753 reaction equation
C(OC(=O)[NH:7][C@@H:8]([CH2:42][C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1)[C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[C:17](=[O:41])[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[C:26][C:27]2[C:28]([C:33]3[CH:38]=[C:37]([CH3:39])[CH:36]=[CH:35][C:34]=3[OH:40])=[N:29][N:30]([CH3:32])[CH:31]=2)=[CH:21][CH:20]=1)=[O:10])(C)(C)C.Cl>CCO>[OH:40][C:34]1[CH:35]=[CH:36][C:37]([CH3:39])=[CH:38][C:33]=1[C:28]1[C:27]([C:26]#[C:25][C:22]2[CH:21]=[CH:20][C:19]([NH:18][C:17]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16][N:11]3[C:9](=[O:10])[C@@H:8]([NH2:7])[CH2:42][C:43]3[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=3)=[O:41])=[CH:24][CH:23]=2)=[CH:31][N:30]([CH3:32])[N:29]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 135974987HCID 135974987, compound

Product 1

HCID 135975028HCID 135975028, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of compound 6 (9.9 g) in EtOH (80 mL) was cooled to 0° C. with ice-water bath. Concentrated hydrochloric acid (37%, 40 mL) was added into the above solution slowly at 0° C. The ice-bath was removed and the mixture was stirred at rt until the reaction was complete as indicated by LCMS (ca. 5 h). A solution of NaHCO3 (40 g) in water (200 mL) was added slowly with stirring. The final mixture was extracted with EtOAc (˜200 mL), and the organic layer was washed with brine and dried over sodium sulfate. It was filtered, and the solvent was removed with rotavapor. The residua was dried under high vacuum to provide the title compound as pale yellow gum-like powder (6.5 g, 77.4%) and was used for next step without further purification. LCMS (ESI) m/z 562.39 (MH+), 259.26 (100); HPLC: tR=5.05 min.

Workup

  1. customThe ice-bath was removed
  2. customas indicated by LCMS (ca. 5 h)
  3. additionA solution of NaHCO3 (40 g) in water (200 mL) was added slowly
  4. stirringwith stirring
  5. extractionThe final mixture was extracted with EtOAc (˜200 mL)
  6. washthe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationIt was filtered
  9. customthe solvent was removed with rotavapor
  10. customThe residua was dried under high vacuum

Sources & evidence

ORD record
ord-1aa05fdc564f42f79765d01cedcb5fbd
Source dataset
uspto-grants-2011_04
Patent number
US07923004B2

Reaction notes

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