Réaction #218281

ord-152e200e3f76433e945e2f5c76c215f4

Équation de réaction

O=C(O)c1ccc2c(c1)Nc1ccccc1S2
intermediate 1.10
O=C(O)c1ccc2c(c1)Nc1ccccc1S2
10H-phenothiazine-2-carboxylic acid
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(C)C
intermediate 1.8
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(C)C
L-leucyl-L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(C)C
L-leucyl-L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide
O=C(O)c1ccc2c(c1)Nc1ccccc1S2
10H-phenothiazine-2-carboxylic acid
→
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)c1ccc2c(c1)Nc1ccccc1S2
yellow solid
Rendement 21.0%
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)c1ccc2c(c1)Nc1ccccc1S2
N-(10H-phenothiazin-2-ylcarbonyl)-L-leucyl-L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide
Rendement 21.0%

Réactifs

O=C(O)c1ccc2c(c1)Nc1ccccc1S2
intermediate 1.10
O=C(O)c1ccc2c(c1)Nc1ccccc1S2
10H-phenothiazine-2-carboxylic acid
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(C)C
intermediate 1.8
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(C)C
L-leucyl-L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide
—
peptide
—
intermediate 1.1
COC1OCC[C@@H]1NC(=O)[C@H](CC(C)C)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](N)CC(C)C
L-leucyl-L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide
O=C(O)c1ccc2c(c1)Nc1ccccc1S2
10H-phenothiazine-2-carboxylic acid

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe reaction product is purified by chromatography on silica (eluent: ethyl acetate/heptane in proportions of 7/3 to 1/1)

Mode opératoire

The experimental protocol of this peptide condensation is the same as that described for the synthesis of intermediate 1.1, this time using 10H-phenothiazine-2-carboxylic acid (intermediate 1.10) and L-leucyl-L-leucyl-N1-[(3S)-2-methoxytetrahydrofuran-3-yl]-L-leucinamide (intermediate 1.8). The reaction product is purified by chromatography on silica (eluent: ethyl acetate/heptane in proportions of 7/3 to 1/1). 228 mg of a yellow solid is obtained with a yield of 21%. Melting point: 164-165° C.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07384933B2uspto-grants-2008_06