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

Participants

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

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04031069
Source dataset	uspto-grants-1977_06
ORD ID	ord-802c40f114c1414983a6b7b924a20ec2
Source note	uspto-grants-1977_06