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

HRID 1294824

反応式

HRID 1294824 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-9c63790266c841a5a98ec1b18deb6e63
出典データセット
uspto-grants-2007_07
特許番号
US07241786B2

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