Hydrochloric Acid → HCID 69483553, compound

HRID 1372452Notes

Reaction equation

HRID 1372452 reaction equation
[CH2:1]([O:8][C:9]([C@@:11]1([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=2)[CH2:15][O:14][C@@H](C(C)(C)C)[N:12]1C=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO.Cl>O>[CH2:1]([O:8][C:9](=[O:10])[C@:11]([NH2:12])([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([C:29]#[N:30])[CH:24]=1)[CH2:15][OH:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 86587419HCID 86587419, compound

Product 1

HCID 69483553HCID 69483553, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 1L round bottom flask equipped with a reflux condenser and a Teflon-coated magnetic stirring bar was charged with compound 2 (30 g, 73.8 mmol) and MeOH (1 L). 6N HCl (45 mL) was added and the slightly cloudy reaction mixture was heated to a gentle reflux with stirring for 48 hours. The reaction mixture was cooled to ambient temperature and concentrated to dryness to give a white colorless solid, which was dissolved in H2O (300 mL) and extracted with CH2Cl2 (50 mL). The aqueous phase was concentrated to give the title compound as a white colorless solid (22.7 g, 89%).

Workup

  1. customthe slightly cloudy reaction mixture
  2. temperaturewas heated to
  3. temperaturea gentle reflux
  4. concentrationconcentrated to dryness
  5. customto give a white colorless solid, which
  6. extractionextracted with CH2Cl2 (50 mL)
  7. concentrationThe aqueous phase was concentrated

Sources & evidence

ORD record
ord-3bb06244eac14c618cbeafa7b8f1b82f
Source dataset
uspto-grants-2007_01
Patent number
US07157596B2

Reaction notes

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