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

関与物質

役割	名称	HCID	仕込み量
反応物	Dicyclohexylcarbodiimide	HCID 10868	—
反応物	N-tert-Butoxycarbonyl-L-tryptophan	HCID 83169	—
反応物	L-Serine, N-[(1,1-dimethylethoxy)carbonyl]-O-(phenylmethyl)-	HCID 90234	—
反応物	O-benzyl-N-((tert-butoxy)carbonyl)-L-tyrosine	HCID 98763	—
反応物	BOC-D-alanine	HCID 637606	—
溶媒	Methanol	HCID 887	—
溶媒	Triethylamine	HCID 8471	—
生成物	Nalpha-t-Butoxycarbonyl-L-tryptophyl-O-benzyl-L-seryl-O-benzyl-L-tyrosyl-D-alanine	HCID 53959304	—

反応手順

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.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US04031069
出典データセット	uspto-grants-1977_06
ORD ID	ord-802c40f114c1414983a6b7b924a20ec2
出典メモ	uspto-grants-1977_06