Triethylamine → HCID 178472519, 화합물

HRID 2242262노트

반응식

HRID 2242262 반응식
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]

참가 물질

8

반응물 4

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

생성물 1

HCID 178472519HCID 178472519, 화합물수율 83%

시약·촉매·용매 3

HCID 176Acetic Acid용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-04f2e2f5cb6945a0a2469ceb0632700a
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07671043B2

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