Acetate → HCID 67852048, compound
Reaction equation
[CH3:1][C:2]([O-:4])=[O:3].[CH:5]1(N=C=[N:13][CH:14]2[CH2:19][CH2:18][CH2:17][CH2:16]C2)CCCC[CH2:6]1.[OH:20]N1C(=O)CCC1=O>O1CCCC1>[C:2]([O:4][CH2:5][CH3:6])(=[O:3])[CH3:1].[N:13]1[CH:14]=[CH:19][CH:18]=[CH:17][C:16]=1[CH2:1][C:2]([OH:4])=[O:3].[OH2:20]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Condensation (two runs) of ##STR106## (mixture of isomers, 31.4 mg., 400 mg.) and H-trp-Leu-Phe-NH2 (example 2, 77.5 mg., 556 mg.) using dicyclohexylcarbodiimide (17.2 mg., 220 mg.) and N-hydroxysuccinimide (9.6 mg., 123 mg.) in tetrahydrofuran (1 ml. 10 ml.) at 0° C. for 0.5 hr. and then at room temperature (overnight, 6 hr.), combination of the crude products, and purification by column chromatography on silica gel first with ethyl acetate-pyridine-acetic acid-water (900:54:16:30) as eluant to give ##STR107## as a mixture of isomers (350 mg., 37% yield) and then with ethyl acetate-pyridine-acetic acid-water (1500:54:16:30) as eluant gave isomer A (75 mg.) and isomer B (125 mg.). Lyophilization of isomer A from acetic acid followed by conversion into the phosphate salt by ion exchange chromatography followed by lyophilization from water-acetic acid (95:5) gave ##STR108## phosphate (1:1) salt as an amorphous pale yellow solid (19 mg.).
Workup
- customat 0° C.
- customfor 0.5 hr
- customand then at room temperature (overnight, 6 hr.), combination of the crude products, and purification by column chromatography on silica gel first with ethyl acetate-pyridine-acetic acid-water (900:54:16:30) as eluant
- customto give ##STR107## as a mixture of isomers (350 mg., 37% yield)
Sources & evidence
- ORD record
- ord-7bb224efddc94819910098963442a1e5
- Source dataset
- uspto-grants-1995_01
- Patent number
- US05378803
Reaction notes
Loading…