Reaction #1885029

ord-b2d1118c55cf45b9bbd93a4874afa558

Reaction equation

CC(C)(C)OC(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O
Boc-Glu(OtBu)-Glu(OtBu)-OSu
CC[C@H](C)[C@H](N)C(=O)O.COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314
Ile Hydrocodone
→
CC[C@H](C)[C@H](NC(=O)[C@H](CCC(=O)O)NC(=O)[C@@H](N)CCC(=O)O)C(=O)O.COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314
Glu-Glu-Ile Hydrocodone

Reactants

CC(C)(C)OC(=O)CC[C@H](NC(=O)OC(C)(C)C)C(=O)N[C@@H](CCC(=O)OC(C)(C)C)C(=O)ON1C(=O)CCC1=O
Boc-Glu(OtBu)-Glu(OtBu)-OSu
—
amino acid
CC[C@H](C)[C@H](N)C(=O)O.COc1ccc2c3c1O[C@H]1C(=O)CC[C@H]4[C@@H](C2)N(C)CC[C@]314
Ile Hydrocodone

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

Glu-Glu-Ile-Hydrocodone was prepared by similar methods except the amino acid starting material was Boc-Glu(OtBu)-Glu(OtBu)-OSu and the conjugate starting material was Ile-Hydrocodone.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08343927B2uspto-grants-2013_01