tert-butyl N-(4-aminobutyl)carbamate → N-t-Butyloxycarbonyl-N'-(3-[2-Chloro-6-Fluorophenyl]-5-Methylisoxazol-4-oyl)-1,4-Diaminobutane

HRID 2228472Notes

Reaction equation

HRID 2228472 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH2:13])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=1[C:22]1[C:26]([C:27](Cl)=[O:28])=[C:25]([CH3:30])[O:24][N:23]=1>>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][CH2:12][NH:13][C:27]([C:26]1[C:22]([C:16]2[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:15]=2[Cl:14])=[N:23][O:24][C:25]=1[CH3:30])=[O:28])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 4351tert-butyl N-(4-aminobutyl)carbamateHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride

Product 1

HCID 18470603N-t-Butyloxycarbonyl-N'-(3-[2-Chloro-6-Fluorophenyl]-5-Methylisoxazol-4-oyl)-1,4-DiaminobutaneYield 100.1%

Procedure

N-t-butyloxycarbonyl-1,4-diaminobutane (985 mg, 5.23 mmol) and 3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-oyl chloride (1.43 g, 5.23 mmol) were converted to 2.23 g of the title compound by the procedure of Preparation 1 except that the reaction time was about 18 hours. (100%). EA calculated for: C20H25N3O4ClF: C, 56.41; H, 5.92; N, 9.87. Found: C, 56.12; H, 5.75; N, 9.67. MS(FD) m/z 426 (M+).

Sources & evidence

ORD record
ord-4f589efdd0cf45e4ad630ff4375e657b
Source dataset
uspto-grants-2002_07
Patent number
US06417193B1

Reaction notes

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