Dicyclohexylcarbodiimide → Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanine

https://huagongshe.com/de/reaction/437688

Beteiligte Stoffe

Rolle	Name	HCID	Einwaage
Edukt	Dicyclohexylcarbodiimide	HCID 10868	—
Edukt	N-tert-Butoxycarbonyl-L-tryptophan	HCID 83169	—
Edukt	L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-	HCID 90234	—
Edukt	O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine	HCID 98763	—
Edukt	BOC-D-alanine	HCID 637606	—
Lösungsmittel	Methanol	HCID 887	—
Lösungsmittel	Triethylamine	HCID 8471	—
Produkt	Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanine	HCID 53959304	—

Reaktionsschritte

Nα-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanine resin is prepared from 23 g., 14 mmol. of Nα-t-butoxycarbonyl-D-alanine resin by successive coupling, according to the general process for solid phase synthesis given in Example 1 with (1) 7 g., 19 mmol, of Nα-t-butoxycarbonyl-O-benzyl-L-tyrosine and 4 g., 19.4 mmol, of dicyclohexylcarbodiimide, (2) 6 g., 19.7 mmol, of Nα-t-butoxycarbonyl-O-benzyl-L-serine and 4 g. of dicyclohexylcarbodiimide, and (3) 6 g., 19.7 mmol, of Nα-t-butoxycarbonyl-L-tryptophan and 4 g. of dicyclohexylcarbodiimide. The resin thus obtained, 30 g., is stirred for 20 hours with 600 ml. of methanol and 50 ml. of triethylamine. The solution is filtered and evaporated. The residue is solidified by trituration in ether; 8 grams; m.p. 93°-94° C.

Herkunft & Nachweise

DOI	10.6084/m9.figshare.5104873.v1
Patentnummer	US04031069
Quelldatensatz	uspto-grants-1977_06
ORD ID	ord-802c40f114c1414983a6b7b924a20ec2
Quellennotiz	uspto-grants-1977_06