Trimethyl orthoacetate → HCID 87212353, compound

HRID 536668Notes

Reaction equation

HRID 536668 reaction equation
[NH2:1][C:2]1[C:13]2[C@@:12]3([CH3:16])[C@H:14]([CH3:15])[C@H:8]([N:9]([C:17](=[O:22])[C:18]([F:21])([F:20])[F:19])[CH2:10][CH2:11]3)[CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[OH:23].[C:24](OC)(OC)(OC)[CH3:25]>>[F:20][C:18]([F:21])([F:19])[C:17]([N:9]1[CH2:10][CH2:11][C@:12]2([CH3:16])[C@H:14]([CH3:15])[C@H:8]1[CH2:7][C:6]1[CH:5]=[CH:4][C:3]3[O:23][CH:24]([CH3:25])[NH:1][C:2]=3[C:13]=12)=[O:22]

Participants

3

Reactant 2

HCID 15050Trimethyl orthoacetateHCID 58123501HCID 58123501, compound

Product 1

HCID 87212353HCID 87212353, compound

Conditions

Temperature
100 °C

Procedure

1-[(2R,6R,11S)-7-Amino-8-hydroxy-6,11-dimethyl-1,2,5,6-tetrahydro-4H-2,6-methano-benzo[d]azocin-3-yl]-2,2,2-trifluoro-ethanone (200 mg) taken up in trimethyl orthoacetate (1 mL) is heated at 100° C. for 3 h. After cooling to ambient temperature, the mixture is concentrated and the residue is triturated with little methanol and dried to give the title compound.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. concentrationthe mixture is concentrated
  3. customthe residue is triturated with little methanol
  4. customdried

Sources & evidence

ORD record
ord-c8bb5561427f407e8f5052039a231860
Source dataset
uspto-grants-2014_10
Patent number
US08859580B2

Reaction notes

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