Hydrochloric Acid → HCID 58109336, compound

HRID 2037543Notes

Reaction equation

HRID 2037543 reaction equation
[NH2:1][CH2:2][CH:3]([OH:35])[CH2:4][C@@:5]1([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[O:10][C:9](=[O:11])[N:8]([C@H:12]([C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][C:21]=3[F:27])=[CH:16][CH:15]=2)[CH3:13])[CH2:7][CH2:6]1.Cl.[NH2:37][C:38](N)=[O:39].C([O-])(O)=O.[Na+]>O.CCO>[F:27][C:21]1[CH:22]=[C:23]([F:26])[CH:24]=[CH:25][C:20]=1[C:17]1[CH:16]=[CH:15][C:14]([C@@H:12]([N:8]2[CH2:7][CH2:6][C@:5]([CH2:4][CH:3]([OH:35])[CH2:2][NH:1][C:38]([NH2:37])=[O:39])([C:28]3[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=3)[O:10][C:9]2=[O:11])[CH3:13])=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 516892Sodium BicarbonateHCID 58109438HCID 58109438, compound

Product 1

HCID 58109336HCID 58109336, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of (6S)-6-(3-amino-2-hydroxypropyl)-3-((S)-1-(2′,4′-difluorobiphenyl-4-yl)ethyl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (300 mg, 0.62 mmol) in H2O (10 mL) was added HCl (12 N, 0.05 mL), urea (372 mg, 6.2 mmol) and EtOH (2 mL). Then the mixture was heated to reflux overnight. The reaction mixture was cooled to rt and adjusted pH to 9˜10 by saturated NaHCO3 solution. The mixture was concentrated and extracted by CH2Cl2. The combined organic layer was dried and concentrated to give the residue, which was purified by preparative HPLC followed by chiral preparative HPLC to give two isomers.

Workup

  1. temperatureThen the mixture was heated
  2. temperatureto reflux overnight
  3. concentrationThe mixture was concentrated
  4. extractionextracted by CH2Cl2
  5. customThe combined organic layer was dried
  6. concentrationconcentrated
  7. customto give the residue, which
  8. customwas purified by preparative HPLC
  9. customto give two isomers

Sources & evidence

ORD record
ord-dcc207f844564acaab5a9764a09a6a22
Source dataset
uspto-grants-2013_11
Patent number
US08575156B2

Reaction notes

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