(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidine → [1-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-pyrrolidin-3(R)-yl]-carbamic acid tert-butyl ester

HRID 550827Notes

Reaction equation

HRID 550827 reaction equation
C1(O[C:8](=[O:21])[NH:9][C:10]2[S:11][C:12]3[N:13]=[CH:14][N:15]=[C:16]([O:19][CH3:20])[C:17]=3[N:18]=2)C=CC=CC=1.[C:22]([O:26][C:27](=[O:34])[NH:28][C@@H:29]1[CH2:33][CH2:32][NH:31][CH2:30]1)([CH3:25])([CH3:24])[CH3:23]>C(#N)C>[C:22]([O:26][C:27](=[O:34])[NH:28][C@@H:29]1[CH2:33][CH2:32][N:31]([C:8](=[O:21])[NH:9][C:10]2[S:11][C:12]3[N:13]=[CH:14][N:15]=[C:16]([O:19][CH3:20])[C:17]=3[N:18]=2)[CH2:30]1)([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 1514397(3R)-(+)-3-(tert-Butoxycarbonylamino)pyrrolidineHCID 59011944(7-Methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl ester

Product 1

HCID 59011933[1-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-pyrrolidin-3(R)-yl]-carbamic acid tert-butyl esterYield 103%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A solution of (7-methoxy-thiazolo[5,4-d]pyrimidin-2-yl)-carbamic acid phenyl ester (1.5 g, 0.0049 mol) in acetonitrile (80 mL) at 25° C. was treated with pyrrolidin-3(R)-yl-carbamic acid tert-butyl ester (0.92 g, 0.049 mol). The reaction mixture was heated at reflux for 1 h. It was then cooled to 25° C. and concentrated in vacuo. The residue was triturated with ether, filtered and dried in vacuo to afford [1-(7-methoxy-thiazolo[5,4-d]pyrimidin-2-ylcarbamoyl)-pyrrolidin-3(R)-yl]-carbamic acid tert-butyl ester (1.99 g, 99%); LRMS for C16H22N6O4S (M+H) at m/z 395.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with ether
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-4a1b592c24d942109d931aadb73f5a4f
Source dataset
uspto-grants-2011_05
Patent number
US07947692B2

Reaction notes

Loading…