Triethylamine → HCID 178472518, compound

HRID 2242259Notes

Reaction equation

HRID 2242259 reaction equation
Cl.[CH2:2]([O:4][C:5]([C@H:7]1[CH2:10][C@@H:9]([NH2:11])[CH2:8]1)=[O:6])[CH3:3].C(N(CC)CC)C.[CH3:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[O:30][N:29]=[C:28]([C:31]3[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=3)[N:27]=2)=[CH:22][CH:21]=1.C([BH3-])#N.[Na+]>CC(O)=O.C1COCC1>[CH2:2]([O:4][C:5]([C@H:7]1[CH2:10][C@@H:9]([NH:11][CH2:35][C:34]2[CH:33]=[CH:32][C:31]([C:28]3[N:27]=[C:26]([C:23]4[CH:24]=[CH:25][C:20]([CH3:19])=[CH:21][CH:22]=4)[O:30][N:29]=3)=[CH:38][CH:37]=2)[CH2:8]1)=[O:6])[CH3:3]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 5003444Sodium cyanoborohydrideHCID 592042754-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehydeHCID 178472514HCID 178472514, compound

Product 1

HCID 178472518HCID 178472518, compoundYield 39,495.398%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of cis-3-amino-cyclobutanecarboxylic acid ethyl ester hydrochloride (50.7 mg, 0.282 mmol), triethylamine (0.058 mL, 0.423 mmol) and THF (2.5 mL) was stirred at room temperature for 30 minutes. 4-[5-(4-Methylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (74.5 mg, 0.282 mmol) and AcOH (0.50 mL) were added to the reaction mixture and stirred for 30 minutes. Sodium cyanoborohydride (35.4 g, 0.563 mmol) was added to the reaction mixture, stirred for 18 hours, quenched with sat. NaHCO3 and extracted with ethyl acetate. The organic phase was concentrated in vacuo. Purification by flash chromatography (silica, 2:8 EtOAc:hexanes) provided the title compound (43.6 g, 39.8% yield) as a solid.

Workup

  1. stirringstirred for 30 minutes
  2. stirringstirred for 18 hours
  3. customquenched with sat. NaHCO3
  4. extractionextracted with ethyl acetate
  5. concentrationThe organic phase was concentrated in vacuo
  6. customPurification by flash chromatography (silica, 2:8 EtOAc:hexanes)

Sources & evidence

ORD record
ord-ef2c1d09dd4d43028376f0050abfad40
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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