Reaction #60628

ord-1a98a909efdd4839a613a93fa2b72903

Reaction equation

CCOC(=O)C(CCC1(C(=O)N[C@H]2CCc3ccccc3N(CC(=O)OC(C)(C)C)C2=O)CCCC1)CC(=O)O

3-{[1-({[(3S)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]ethyl}-4-ethoxy-4-oxobutyric acid

COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1.Cl

[ 2 ]

Adriamycin

→

CCOC(=O)C(CC(=O)NC(C)C)CC1(C(=O)N[C@H]2CCc3ccccc3N(CC(=O)OC(C)(C)C)C2=O)CCCC1

Ethyl 2-{[(3S)-1-({[1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]methyl}-4-(isopropylamino)-4-oxobutyrate

Reactants

—

[ 1 ]

3-{[1-({[(3S)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]ethyl}-4-ethoxy-4-oxobutyric acid

Reagents

None

Solvents

methanol

Conditions

Detailed conditions

See reaction.notes.procedure_details.

Workup

1
OtherWith a retention time of 6.5 min., there was obtained 33 g of the second stereoisomer, which

Procedure

With a retention time of 6.5 min., there was obtained 33 g of the second stereoisomer, which was assigned the designation “rel2” in relation to the chiral center “*Ca” bearing the group “—COOR1”, as (2“rel2”)-3-{[1-({[(3S)-1-(2-tert.butoxy-2-oxoethyl)-2-oxo-2,3,4,5-tetrahydro-1H-1-benzazepin-3-yl]amino}carbonyl)cyclopentyl]ethyl}-4-ethoxy-4-oxobutyric acid, 1H-NMR (CDCl3): 7.31-7.17, m, [3]; 7.11, d, [2]; 6.81, d, [1]; 4.60, 4.56, 4.35, 4.31, AB-Q. [2]; 4.48, m, [1]; 4.10, m, [1]; [α]D=−136° (1% in methanol).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07427611B2uspto-grants-2008_09