Toluene → [1-(5-Tert-butyl-isoxazol-3-ylcarbamoyl)butyl]-carbamic acid tert-butyl ester

HRID 1294824

반응식

HRID 1294824 반응식
Cl.[C:2]([C:6]1[O:10][N:9]=[C:8]([NH2:11])[CH:7]=1)([CH3:5])([CH3:4])[CH3:3].C1(C)C=CC=CC=1.C[O:20][C:21](=O)[CH:22]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:24][CH3:25]>C1COCC1>[C:30]([O:29][C:27](=[O:28])[NH:26][CH:22]([C:21](=[O:20])[NH:11][C:8]1[CH:7]=[C:6]([C:2]([CH3:5])([CH3:4])[CH3:3])[O:10][N:9]=1)[CH2:23][CH2:24][CH3:25])([CH3:31])([CH3:32])[CH3:33]

참가 물질

5

반응물 3

HCID 1140TolueneHCID 119695193-Isoxazolamine, 5-(1,1-dimethylethyl)-, hydrochloride (1:1)HCID 232782002-Tert-butoxycarbonylamino-pentanoic acid methyl ester

생성물 1

HCID 69419406[1-(5-Tert-butyl-isoxazol-3-ylcarbamoyl)butyl]-carbamic acid tert-butyl ester수율 141.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 5-tert-butyl-isoxazol-3-ylamine hydrochloride (1.22 g, 8.69 mmol) in THF was added 2 M AIMe3 in toluene (4.3 ml, 8.6 mmol) at room temperature and stirred for 1 hr. A solution of 2-tert-butoxycarbonylamino-pentanoic acid methyl ester (1.005 g, 4.34 mmol) in THF was added and the resulting mixture was stirred at room temperature over the weekend. The mixture was quenched with Rochelle salt and extracted with ethyl acetate. The organic layer was separated, dried and concentrated to give 2.08 g of the title compound as a crude oil. The oil was purified by silica gel column chromatography using 1% methanl in methylenechloride as eluent to give the title compound as a white solid (0.554 g). 1H NMR (CDCl3) □ 8.8 (brs, 1H), 6.7 (s, 1H), 4.85 (brs, 1H), 4.22 (m, 1H), 1.9 (m, 1H), 1.4-1.7 (m, 3H), 1.45 (s, 9H), 1.44 (s, 9H), 0.97 (t, 3H) ppm. LC-MS M+1=340.3.

후처리

  1. stirringthe resulting mixture was stirred at room temperature over the weekend
  2. customThe mixture was quenched with Rochelle salt
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. customdried
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-9c63790266c841a5a98ec1b18deb6e63
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241786B2

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