tert-butyl N-(pyrrolidin-3-yl)carbamate → HCID 20268140, compound

HRID 1719356Notes

Reaction equation

HRID 1719356 reaction equation
[F:1][C:2]1[C:3](F)=[C:4]2[O:9][CH2:8][C:7](=[CH2:10])[N:6]3[CH:11]=[C:12]([C:17]([OH:19])=[O:18])[C:13](=[O:16])[C:14]([CH:15]=1)=[C:5]23.[C:21]([O:25][C:26]([NH:28][CH:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)=[O:27])([CH3:24])([CH3:23])[CH3:22]>CS(C)=O>[C:21]([O:25][C:26]([NH:28][CH:29]1[CH2:33][CH2:32][N:31]([C:3]2[C:2]([F:1])=[CH:15][C:14]3[C:13](=[O:16])[C:12]([C:17]([OH:19])=[O:18])=[CH:11][N:6]4[C:7](=[CH2:10])[CH2:8][O:9][C:4]=2[C:5]=34)[CH2:30]1)=[O:27])([CH3:24])([CH3:22])[CH3:23]

Participants

4

Reactant 2

HCID 2757234tert-butyl N-(pyrrolidin-3-yl)carbamateHCID 13491392HCID 13491392, compound

Product 1

HCID 20268140HCID 20268140, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

130 mg of 9,10-difluoro-3-methylene-7-oxo-2,3-dihydro-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid and 300 mg of 3-tertiary-butoxycarbonylaminopyrrolidine were added to 3 ml of dimethyl sulfoxide and the mixture was allowed to react for 3 hours at 100°-110° C. (bath temperature). The solvent was distilled off in vacuo. The residue was washed with diethyl ether and purified by silica gel column chromatography and then recrystallized from benzene to give 125 mg of 10-(3-tertiary-butoxycarbonylamino-1-pyrrolidinyl)-9-fluoro-3-methylene-7-oxo-2,3-dihydro-7H-pyrido(1,2,3-de)-1,4-benzoxazine-6-carboxylic acid with mp 219°-220° C. as luster yellow crystals.

Workup

  1. customto react for 3 hours at 100°-110° C. (bath temperature)
  2. distillationThe solvent was distilled off in vacuo
  3. washThe residue was washed with diethyl ether
  4. custompurified by silica gel column chromatography
  5. customrecrystallized from benzene

Sources & evidence

ORD record
ord-7ae9b54e0e884e479705b3962f3b692f
Source dataset
uspto-grants-1985_09
Patent number
US04539401

Reaction notes

Loading…