HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Cesium carbonate → 1-{2-Chloro-5-[(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid tert-butyl ester

HRID 1629748
Notes
Print preview

Reaction equation

HRID 1629748 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[C:17](Br)[CH:16]=[CH:15][C:14]=2[Cl:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:21][C:22]1[C:27]([CH3:28])=[CH:26][C:25]([C@H:29]([NH2:32])[CH2:30][CH3:31])=[CH:24][C:23]=1[CH3:33].C(=O)([O-])[O-].[Cs+].[Cs+].CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C>C1(C)C=CC=CC=1.C(O)(C)(C)C.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:1]([O:5][C:6]([CH:8]1[CH2:11][N:10]([CH2:12][C:13]2[CH:18]=[C:17]([NH:32][C@@H:29]([C:25]3[CH:24]=[C:23]([CH3:33])[C:22]([Cl:21])=[C:27]([CH3:28])[CH:26]=3)[CH2:30][CH3:31])[CH:16]=[CH:15][C:14]=2[Cl:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 55278509(R)-1-(4-Chloro-3,5-dimethyl-phenyl)-propylamineHCID 583744221-(5-Bromo-2-chloro-benzyl)azetidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 67346198
1-{2-Chloro-5-[(R)-1-(4-chloro-3,5-dimethyl-phenyl)-propylamino]-benzyl}-azetidine-3-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolventHCID 6386tert-ButanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of INT 57 (250 mg, 0.693 mmol), amine INT 38 (137 mg, 0.693 mmol) and cesium carbonate (678 mg, 2.079 mmol) in toluene (4.5 mL) and tert-butanol (1.8 mL) was purged with argon for 10 minutes. Then, XPhos (66.1 mg, 0.139 mmol) and palladium acetate (15.56 mg, 0.069 mmol) were added, the vial was closed and heated at 100° C. for 3 hours. The reaction mixture was then diluted with EtOAc (35 mL) and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and concentrated.

Workup

  1. customwas purged with argon for 10 minutes
  2. customthe vial was closed
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-0848c373235b465daf2e8b4a7bf06181
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08791100B2

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes