Sodium Carbonate → HCID 68175329, compound

HRID 408613Notes

Reaction equation

HRID 408613 reaction equation
[C:1]1(B(O)O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:16][C:17]1[CH:42]=[CH:41][C:20]([CH2:21][N:22]([CH3:40])[C:23]([C:25]2([CH3:39])[CH2:28][CH2:27][N:26]2[C:29](=[O:38])[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33](I)[CH:32]=2)=[O:24])=[CH:19][CH:18]=1>O1CCOCC1.O>[Cl:16][C:17]1[CH:42]=[CH:41][C:20]([CH2:21][N:22]([CH3:40])[C:23]([C:25]2([CH3:39])[CH2:28][CH2:27][N:26]2[C:29](=[O:38])[CH2:30][C:31]2[CH:32]=[C:33]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:34]=[CH:35][CH:36]=2)=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 86702030HCID 86702030, compound

Product 1

HCID 68175329HCID 68175329, compound

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

To a solution of phenyl boronic acid (1.5 eq.) in Dioxane/H2O (9/1) were added Na2CO3 (4 eq.) and 1-[2-(3-iodo-phenyl)-acetyl]-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-methyl-amide, compound 8 (1 eq.). The flask was evacuated and backfilled with argon. Then Pd(PPh3)4 was added and the reaction was heated at 90° C. until completion. The crude was partitioned between water and EtOAc. The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated under reduced pressure. The crude was purified by chromatography on silica gel (elution with Heptane/EtOAc: 100/0 to 20/80) to afford 1-(2-biphenyl-3-yl-acetyl)-2-methyl-azetidine-2-carboxylic acid (4-chloro-benzyl)-methyl-amide.

Workup

  1. customThe flask was evacuated
  2. additionThen Pd(PPh3)4 was added
  3. customThe crude was partitioned between water and EtOAc
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude was purified by chromatography on silica gel (elution with Heptane/EtOAc: 100/0 to 20/80)

Sources & evidence

ORD record
ord-97276dbba9164445a4e1df3663b44dea
Source dataset
uspto-grants-2014_06
Patent number
US08759334B2

Reaction notes

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