Triethylamine → HCID 178472519, compound

HRID 2242262Notes

Reaction equation

HRID 2242262 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.[CH2:19]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[O:33][N:32]=[C:31]([C:34]3[CH:35]=[C:36]([CH:39]=[CH:40][CH:41]=3)[CH:37]=O)[N:30]=2)=[CH:25][CH:24]=1)[CH:20]([CH3:22])[CH3:21].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(OCC)(=O)C.C(O)(=O)C.C1COCC1>[CH2:2]([O:4][C:5]([C@H:7]1[CH2:10][C@@H:9]([NH:11][CH2:37][C:36]2[CH:39]=[CH:40][CH:41]=[C:34]([C:31]3[N:30]=[C:29]([C:26]4[CH:27]=[CH:28][C:23]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:24][CH:25]=4)[O:33][N:32]=3)[CH:35]=2)[CH2:8]1)=[O:6])[CH3:3]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 592043053-[5-(4-Isobutylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehydeHCID 178472514HCID 178472514, compound

Product 1

HCID 178472519HCID 178472519, compoundYield 83%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of cis-3-amino-cyclobutanecarboxylic acid ethyl ester hydrochloride (34 mg, 0.189 mmol), triethyl amine (39.5 uL, 0.284 mmol) and THF (1.7 mL) was stirred at ambient temperature for 30 minutes. Acetic acid (300 uL) and 3-[5-(4-isobutylphenyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (58 mg, 0.189 mmol) were added to the reaction mixture and stirred for 30 minutes. Sodium triacetoxy borohydride (80 mg, 0.379 mmol) was added to the mixture and stirred for 18 hours. The reaction was diluted with ethyl acetate, washed with saturated sodium bicarbonate and the organic layer was separated and concentrated in vacuo. Purification by flash chromatography (silica, 1:99 to 1:9 MeOH:chloroform) provided the title compound (68 mg, 83% yield) as a solid.

Workup

  1. stirringstirred for 18 hours
  2. washwashed with saturated sodium bicarbonate
  3. customthe organic layer was separated
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography (silica, 1:99 to 1:9 MeOH:chloroform)

Sources & evidence

ORD record
ord-04f2e2f5cb6945a0a2469ceb0632700a
Source dataset
uspto-grants-2010_03
Patent number
US07671043B2

Reaction notes

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