Réaction #2174242

ord-78e5f662f52240529c6c5f68b3d647b7

Équation de réaction

COC1C(OC(C(NCCCNC(=O)C(NC(=O)C(NC(=O)NC(C(=O)O)C(C)C)C2CCNC(=N)N2)C(O)C(C)C)C(=O)O)C2OC(n3ccc(=O)[nH]c3=O)C(O)C2O)OC(CN)C1O
16-({[5-(aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11,15-pentaazaheptadecane-1,17-dioic acid
CCCCCCN=C=O
hexylisocyanate
→
CCCCCCN1C(=O)C([C@@H](OC2O[C@H](CN)[C@H](O)[C@H]2OC)[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)N(CCCNC(=O)C(NC(=O)C(NC(=O)NC(C(=O)O)C(C)C)C2CCNC(=N)N2)C(O)C(C)C)C1=O
desired product
Rendement 56.9%
CCCCCCN1C(=O)C([C@@H](OC2O[C@H](CN)[C@H](O)[C@H]2OC)[C@H]2O[C@@H](n3ccc(=O)[nH]c3=O)[C@H](O)[C@@H]2O)N(CCCNC(=O)C(NC(=O)C(NC(=O)NC(C(=O)O)C(C)C)C2CCNC(=N)N2)C(O)C(C)C)C1=O
14-[5-((R)-{[(3R,4S,5R)-5-(Aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{(2S,3S,4R,5R)-5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-3-hexyl-2,4-dioxo-1-imidazolidinyl]-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11-tetraazatetradecan-1-oic acid
Rendement 56.9%

Réactifs

COC1C(OC(C(NCCCNC(=O)C(NC(=O)C(NC(=O)NC(C(=O)O)C(C)C)C2CCNC(=N)N2)C(O)C(C)C)C(=O)O)C2OC(n3ccc(=O)[nH]c3=O)C(O)C2O)OC(CN)C1O
16-({[5-(aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11,15-pentaazaheptadecane-1,17-dioic acid
CCCCCCN=C=O
hexylisocyanate

Réactifs

Aucun

Solvants

c1ccncc1
pyridine
CC(=O)CC(C)=O
2,4-pentanedione
CO
methanol

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe title compound is prepared by the procedure of Example 1

Mode opératoire

The title compound is prepared by the procedure of Example 1, using 47.3 mg (50 μmol) of 16-({[5-(aminomethyl)-4-hydroxy-3-methoxytetrahydro-2-furanyl]oxy}{5-[2,4-dioxo-3,4-dihydro-1 (2H)-pyrimidinyl]-3,4-dihydroxytetrahydro-2-furanyl}methyl)-9-(1-hydroxy-2-methylpropyl)-6-(2-iminohexahydro-4-pyrimidinyl)-2-isopropyl-4,7,10-trioxo-3,5,8,11,15-pentaazaheptadecane-1,17-dioic acid (λmax nm in water=259) in 3.0 ml of methanol, 200 μl of pyridine, 200 μl of 2,4-pentanedione and 50 μmol of hexylisocyanate to give 15 mg of the desired product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US06727232B2uspto-grants-2004_04