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

HRID 1294824

Reaction equation

HRID 1294824 reaction equation
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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9c63790266c841a5a98ec1b18deb6e63
Source dataset
uspto-grants-2007_07
Patent number
US07241786B2

Linked notes

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