Dimethylformamide → 6-Aminohexanoic Acid
Reaction equation
ON1[C:6](=[O:7])[C:5](N2C(=O)CCC2=O)=[C:4]([CH2:15][C:16]2(NC(=O)CCCCC)CCCC[C:17]2([NH:30]C(=O)CCCCC)NC(=O)CCCCC)C1=O.CN(C)C=[O:50]>>[NH2:30][CH2:17][CH2:16][CH2:15][CH2:4][CH2:5][C:6]([OH:7])=[O:50]Participants
Procedure
An N-hydroxysuccinimidyltricaproamidocyclohexylmethylmaleimide, a compound having the structure of FIG. 14 of the attached drawings where Z has the structure of FIG. 3, Z' has the structure of FIG. 11, n is 3, and C6H10 is 1,4-cyclohexyl, was then produced from a solution of 100 mg N-hydroxysuceinimidyldicaproamidocyclohexylmethylmaleimide in 2 ml dry dimethylformamide, 23.4 mg 6-aminocaproic acid and 40.5 mg dicyelohexylearbodiimide. A nitrogen atmosphere was established in a flask above the N-hydroxysuccinimidyldicaproamidocyclohexylmethylmaleimide solution, and the 6-aminocaproie acid was added to the flask. The reaction mixture was then stirred under nitrogen at room temperature of about 22° for 16 hours, after which time the dieyclohexylcarbodiimide was added to the flask. Stirring at room temperature was continued for an additional 6 hours, after which time dicyclohexylurea which had precipitated was removed from the reaction mixture by filtration, and the dimethylformamide was evaporated under reduced pressure from the filtrate. A tacky solid which remained was purified by flash chromatography on silica gel (10v/v methanol in chloroform), yielding 60 mg of the N-hydroxysuccinimidyltricaproamidocyclohexylmethylmaleimide, a white solid which has the indicated formula.
Sources & evidence
- ORD record
- ord-8b67847f5c3c4c5f9160264ad501cac9
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05380873
Reaction notes
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