Acetic Acid → (S)-6-(2-Hydroxy-2-methyl-propyl)-3-{(S)-1-[4-(2-methyl-3H-benzoimidazol-5-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one

HRID 80974Notes

Reaction equation

HRID 80974 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[CH:13][C:12]([C@@H:15]([N:17]3[CH2:22][CH2:21][C@:20]([CH2:29][C:30]([OH:33])([CH3:32])[CH3:31])([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[O:19][C:18]3=[O:34])[CH3:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[NH2:8].[C:35](O)(=O)[CH3:36]>>[OH:33][C:30]([CH3:31])([CH3:32])[CH2:29][C@@:20]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[O:19][C:18](=[O:34])[N:17]([C@H:15]([C:12]2[CH:11]=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][C:7]4[N:8]=[C:35]([CH3:36])[NH:1][C:2]=4[CH:3]=3)=[CH:14][CH:13]=2)[CH3:16])[CH2:22][CH2:21]1

Participants

3

Reactant 2

HCID 176Acetic AcidHCID 58109723HCID 58109723, compound

Product 1

HCID 42605721(S)-6-(2-Hydroxy-2-methyl-propyl)-3-{(S)-1-[4-(2-methyl-3H-benzoimidazol-5-yl)-phenyl]-ethyl}-6-phenyl-[1,3]oxazinan-2-one

Conditions

Temperature
150 °C

Procedure

3-[(S)-1-(3′,4′-Diamino-biphenyl-4-yl)-ethyl]-(S)-6-(2-hydroxy-2-methyl-propyl)-6-phenyl-[1,3]oxazinan-2-one (120 mg) taken up in acetic acid (2 mL) was stirred under microwave irradiation at 150° C. for 30 min. After cooling to ambient temperature, the mixture was concentrated under reduced pressure and the residue was purified by HPLC on reversed phase (MeCN/H2O) to afford the title compound.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customthe residue was purified by HPLC on reversed phase (MeCN/H2O)

Sources & evidence

ORD record
ord-21e24409d29342df94ed1ceaabf56ebe
Source dataset
uspto-grants-2014_09
Patent number
US08846668B2

Reaction notes

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