Reaction #816390

ord-8aee28718bec4e0d8343cede1eb5eb25

Reaction equation

COC(=O)[C@@]12O[C@@H](CNC(=O)CNC(=O)CN3CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC3)[C@@H](O)[C@@H]1OC(C)(C)O2
19a
COC(=O)[C@@]12O[C@@H](CNC(=O)CNC(=O)CN3CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC3)[C@@H](O)[C@@H]1OC(C)(C)O2
methyl (3aR,5S,6R,6aS)-6-hydroxy-2,2-dimethyl-5-{[(N-{[4,7,10-tris(2-tert-butoxy-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1-yl]acetyl}glycyl)amino]methyl}dihydrofuro[2,3-d][1,3]dioxole-3a(5H)-carboxylate
O.[Li][OH]
LiOH.H2O
→
CC(C)(C)OC(=O)CN1CCN(CC(=O)NCC(=O)NC[C@@H]2O[C@@]3(C(=O)O)OC(C)(C)O[C@H]3[C@@H]2O)CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1
Product 20a
Yield 81.0%
CC(C)(C)OC(=O)CN1CCN(CC(=O)NCC(=O)NC[C@@H]2O[C@@]3(C(=O)O)OC(C)(C)O[C@H]3[C@@H]2O)CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC1
(3aR,5S,6R,6aS)-6-hydroxy-2,2-dimethyl-5-{[(N-{[4,7,10-tris(2-tert-butoxy-2-oxoethyl)-1,4,7,10-tetraazacyclododecan-1-yl]acetyl} glycyl)amino]methyl}dihydrofuro[2,3-d][1,3]dioxole-3a(5H)-carboxylic acid
Yield 81.0%

Reactants

COC(=O)[C@@]12O[C@@H](CNC(=O)CNC(=O)CN3CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC3)[C@@H](O)[C@@H]1OC(C)(C)O2
19a
COC(=O)[C@@]12O[C@@H](CNC(=O)CNC(=O)CN3CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CCN(CC(=O)OC(C)(C)C)CC3)[C@@H](O)[C@@H]1OC(C)(C)O2
methyl (3aR,5S,6R,6aS)-6-hydroxy-2,2-dimethyl-5-{[(N-{[4,7,10-tris(2-tert-butoxy-2-oxoethyl)-1,4,7,10-tetraazacyclododecane-1-yl]acetyl}glycyl)amino]methyl}dihydrofuro[2,3-d][1,3]dioxole-3a(5H)-carboxylate
O.[Li][OH]
LiOH.H2O

Reagents

None

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    OtherSolvents were evaporated
  2. 2
    Otherthe residue was purified by silica column chromatography

Procedure

To a solution of 19a (1.0 g, 1.17 mmol) in MeOH (2 mL) was added a solution of LiOH.H2O (48.5 mg, 1.17 mmol, Aldrich). The resulting solution was stirred at room temperature for 4 h. Solvents were evaporated and the residue was purified by silica column chromatography. Product 20a was obtained as a white solid (0.8 g; yield 81%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07582280B2uspto-grants-2009_09