Diisopropylethylamine → HCID 68422188, compound

HRID 1713517Notes

Reaction equation

HRID 1713517 reaction equation
[C:1]1([C:7]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:11]3[CH2:12][NH:13][CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(C(C)C)CC)(C)C.[C:32](Cl)(=[O:41])[O:33][C:34]1[CH:39]=[CH:38][C:37]([F:40])=[CH:36][CH:35]=1>O1CCCC1>[F:40][C:37]1[CH:38]=[CH:39][C:34]([O:33][C:32]([N:13]2[CH2:14][CH2:15][N:10]3[C:9](=[O:16])[O:8][C:7]([C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[CH:11]3[CH2:12]2)=[O:41])=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27332564-Fluorophenyl chloroformateHCID 231218811,1-Diphenyltetrahydro-1H-oxazolo[3,4-a]pyrazin-3(5H)-one

Product 1

HCID 68422188HCID 68422188, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of hexahydro-1,1-diphenyl-3H-oxazolo[3,4-a]pyrazin-3-one (50 mg, 0.17 mmol) in tetrahydrofuran (2 mL) were sequentially added diisopropylethylamine (0.30 mL, 1.7 mmol) and 4-fluorophenyl chlorocarbonate (45 mg, 0.26 mmol), and the mixture was stirred at room temperature for 2 hours. The reaction solution was concentrated, and the residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1) and crystallized from diisopropyl ether to obtain the title compound (58 mg, yield 79%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. customthe residue was purified with silica gel column chromatography (hexane:ethyl acetate=3:1)
  3. customcrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-4c89bd1be3fa4f93bf818ee7a7c6774e
Source dataset
uspto-grants-2010_09
Patent number
US07795267B2

Reaction notes

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