Diisopropylethylamine → HCID 59361421, compound

HRID 888867Notes

Reaction equation

HRID 888867 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[N:11]1[C:14](=[O:15])[C:13]([CH3:17])([CH3:16])[NH:12]1)[CH2:8]2.[F:18][C:19]1[C:20]([CH3:28])=[C:21]([CH:25]=[CH:26][CH:27]=1)[C:22](O)=[O:23].C(N(C(C)C)CC)(C)C.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>ClCCl.O>[F:18][C:19]1[C:20]([CH3:28])=[C:21]([C:22]([N:12]2[C:13]([CH3:17])([CH3:16])[C:14](=[O:15])[N:11]2[CH:2]2[CH:3]3[CH2:4][CH:5]4[CH2:6][CH:7]([CH2:8][CH:1]2[CH2:10]4)[CH2:9]3)=[O:23])[CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2466823-Fluoro-2-methylbenzoic acidHCID 2724699PyBOPHCID 673028822-(Adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one

Product 1

HCID 59361421HCID 59361421, compoundYield 8.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(adamantan-2-yl)-4,4-dimethyl-1,2-diazetidin-3-one (50.0 mg, 0.213 mmol) prepared in Process 3 of Example 12 in dichloromethane was added with 3-fluoro-2-methylbenzoic acid (32.8 mg, 0.213 mmol), diisopropylethylamine (82.6 mg, 0.639 mmol) and PyBOP (133 mg, 0.256 mmol) at room temperature, and the resultant was stirred at the same temperature for 18 hours. The reaction solution was added with water and extracted with chloroform. The organic layer was dried over anhydrous sodium sulfate, concentrated in vacuo, the obtained residue was purified using Preparative Thin-Layer chromatography (hexane:ethyl acetate=2:1), and the title compound (6.90 mg, 8.70%) was obtained as a white crystalline solid.

Workup

  1. extractionextracted with chloroform
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customthe obtained residue was purified

Sources & evidence

ORD record
ord-859208e37eb7448086b1caaab2aea1eb
Source dataset
uspto-grants-2012_08
Patent number
US08252781B2

Reaction notes

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