Réaction #11069

ord-87b4f71a3c464d95bdbbcf9b03be006a

Équation de réaction

CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
intermediate 19a
CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
3-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid tert-butyl ester
ClCCl.O=C(O)C(F)(F)F
TFA CH2Cl2
→
CC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
intermediate 19b
Rendement 105.5%
CC1(C(=O)O)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
3-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid
Rendement 105.5%

Réactifs

CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
intermediate 19a
CC(C)(C)OC(=O)C1(C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
3-benzyloxycarbonylamino-6-methyl-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid tert-butyl ester
ClCCl.O=C(O)C(F)(F)F
TFA CH2Cl2

Réactifs

O
water

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ConcentrationThe mixture was concentrated in vacuo

Mode opératoire

A solution of intermediate 19a (55 mg, 0.138 mmol) in 4 mL 1:1 TFA/CH2Cl2 with 2 drops water was stirred at rt for 12 h. The mixture was concentrated in vacuo, then coevaporated with CCl4 to afford 50 mg of intermediate 19b (quantitative), which was used without further purification in the following step.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07094783B2uspto-grants-2006_08