Réaction #11070

ord-7977f68c4da0489ebc38176d5555ba59

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
CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
intermediate 1g
CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
tert-butyl (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylate
C=CCI
allyl iodide
→
C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
intermediate 20a
Rendement 55.0%
C=CCC1(C(=O)OC(C)(C)C)CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
6-allyl-3-benzyloxycarbonylamino-4-oxo-4,6,7,8-tetrahydro-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid tert-butyl ester
Rendement 55.0%

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
CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
intermediate 1g
CC(C)(C)OC(=O)[C@@H]1CCc2ncc(NC(=O)OCc3ccccc3)c(=O)n21
tert-butyl (S)-3-{[(benzyloxy)carbonyl]amino}-4-oxo-4,6,7,8-tetrahydropyrrolo[1,2-a]pyrimidine-6-carboxylate
C=CCI
allyl iodide

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

According to the procedure for the preparation of intermediate 19a, alkylation of intermediate 1g (250 mg, 0.649 mmol) with allyl iodide afforded 153 mg (55%) of intermediate 20a. MS (ESI) 426.4 (M+H+), 448.4 (M+Na+).

Source

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