(-)-Mandelic acid → HCID 131727233, compound

HRID 2376624Notes

Reaction equation

HRID 2376624 reaction equation
[NH2:1][CH:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:13])[C:3]1=[O:14].[C:15]([OH:25])(=[O:24])[C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:17].NC1C2C=CC=CC=2CCN(C)C1=O.C(OC(C)C)(=O)C>C(OC(C)C)(=O)C.C(O)(C)C.[N+](C1C=C(C=O)C(O)=CC=1)([O-])=O>[C:15]([OH:25])(=[O:24])[C@@H:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[OH:17].[NH2:1][C@H:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[CH2:6][CH2:5][N:4]([CH3:13])[C:3]1=[O:14]

Participants

7

Reactant 3

HCID 11914(-)-Mandelic acidHCID 210725651-Amino-3-methyl-1,3,4,5-tetrahydro-2H-3-benzazepin-2-oneHCID 69249854HCID 69249854, compound

Product 1

HCID 131727233HCID 131727233, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 668085-NitrosalicylaldehydeCatalystHCID 3776IsopropanolSolventHCID 7915Isopropyl AcetateSolvent

Conditions

Temperature
45 °C

Procedure

1-Amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one (31.9 g, 168 mmol) was slurried in about 300 mL isopropyl acetate and heated to 45° C. In a separate flask, (R)-(−)-D-mandelic acid (25.0 g, 164 mmol) was heated in about 130 mL of isopropyl alcohol until a solution formed and was added to the 1-amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one/isopropyl acetate slurry obtained above to give a solution from which a precipitate quickly formed. The mixture was stirred at 45° C. for about 3 hours. 5-Nitrosalicylaldehyde (2-hydroxy-5-nitrobenzaldehyde) (1.40 g, 8.38 mmol, 5 mol %) was added to the warm solution and the mixture was stirred at 45° C. After about 14 hours, the slurry was cooled to ambient temperature and stirred for 2 hours before the solids were collected by filtration and rinsed with 70 mL of cold isopropyl acetate, and dried in the vacuum oven at 40° C. to obtain 46.62 g of (S)-1-amino-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepin-2-one (R)-mandelic acid salt (82.9% yield, 98.4% ee).

Workup

  1. customformed
  2. customobtained above
  3. customto give a solution from which a precipitate
  4. customquickly formed
  5. stirringthe mixture was stirred at 45° C
  6. waitAfter about 14 hours
  7. temperaturethe slurry was cooled to ambient temperature
  8. stirringstirred for 2 hours before the solids
  9. filtrationwere collected by filtration
  10. washrinsed with 70 mL of cold isopropyl acetate
  11. customdried in the vacuum oven at 40° C.

Sources & evidence

ORD record
ord-d6ca8debbed348ed95b4b568ddbb5cee
Source dataset
uspto-grants-2008_12
Patent number
US07468365B2

Reaction notes

Loading…