Diisopropylethylamine → 4-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-tert-butoxycarbonyl-3-piperidinol

HRID 1392410

반응식

HRID 1392410 반응식
[NH2:1][CH:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH:3]1[OH:15].[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([NH:23][C:24]1([C:30](O)=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22].OC1C2N=NNC=2C=CC=1.C(N(C(C)C)CC)(C)C.Cl.CN(C)CCCN=C=NCC>CN(C)C=O.C(OCC)(=O)C>[O:16]1[CH:20]=[CH:19][CH:18]=[C:17]1[C:21]([NH:23][C:24]1([C:30]([NH:1][CH:2]2[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[O:9])[CH2:4][CH:3]2[OH:15])=[O:31])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)=[O:22]

참가 물질

8

반응물 5

HCID 81531DiisopropylethylamineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 174552541-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acidHCID 21874161tert-Butyl 4-amino-3-hydroxypiperidine-1-carboxylateHCID 178418300HCID 178418300, 화합물

생성물 1

HCID 693103074-[N-[1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarbonyl]amino]-1-tert-butoxycarbonyl-3-piperidinol수율 46.8%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

반응 조건

온도
0 °C

실험 절차

To the solution of tert-butyl 4-amino-3-hydroxypiperidin-1-carboxylate (20 g, 92 mmol) obtained in step 4 of Preparation Example 1 and 1-[N-(furan-2-ylcarbonyl)amino]cyclohexanecarboxylic acid (5.0 g) obtained in Step 2 in 70 ml of dimethylformamide, were added hydroxybenzotriazole(HOBt; 3.1 g, 23.1 mmol) and diisopropylethylamine (DIEA; 9.0 ml, 53.4 mmol). The reaction mixture was cooled to 0° C. and was added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC-HCl; 5.1 g, 26.7 mmol) thereto. The reaction mixture was stirred for 4 hours at room temperature. The reaction mixture was diluted with 200 ml of ethyl acetate, washed with 10% citric acid solution, a saturated sodium bicarbonate solution and brine. The resulting organic layer was dried and concentrated on sodium sulfate. The resulting residue was purified with column chromatography to give 4.3 g of the titled compound.

후처리

  1. washwashed with 10% citric acid solution
  2. customThe resulting organic layer was dried
  3. concentrationconcentrated on sodium sulfate
  4. customThe resulting residue was purified with column chromatography

출처 및 근거

ORD 기록
ord-291cd657b84a4673b29f111b98368e45
출처 데이터셋
uspto-grants-2008_03
특허 번호
US07342027B2

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