Dicyclohexylcarbodiimide → HCID 54311645, compound

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	HCID 54543957	HCID 54543957	—
Solvent	Methanol	HCID 887	—
Product	HCID 54311645	HCID 54311645	—

Reaction Steps

Nα -t-Butoxycarbonyl-L-tryptophyl-L-prolyl-L-prolyl-O-benzyl-L-tyrosyl-O-benzyl-L-serine resin, 20 g., (24 mmol) is converted to the methyl ester by the procedure of Example 1 yielding the above named product in the form of a glass [α]D23 -68° (c. 1.05 in methanol). The above resin is prepared according to the procedure of Example 1using Nα -t-butoxycarbonyl-O-benzyl-L-serine resin which is successively reacted with 1) 8.9 g. (24 mmol) of Nα -t-butoxycarbonyl-O-benzyl-L-tyrosine and 5 g. (24.2 mmol) of dicyclohexylcarbodiimide, 2) 5.0 g. (23.2 mmol) of Nα -t-butoxycarbonyl-L-proline and 5.0 g, of dicyclohexylcarbodiimide, 3) 5 g. (23.2 mmol) of Nα -t-butoxycarbonyl-L-proline and 5.0 g. of dicyclohexylcarbodiimide and 4) 7.30 g. (24 mmol) of Nα -t-butoxycarbonyl-L-tryptophane and 5 g. (23.2 mmol) dicyclohexylcarbodiimide.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US04043993
Source dataset	uspto-grants-1977_08
ORD ID	ord-d7e1355655894a92b219f2d829c26232
Source note	uspto-grants-1977_08