(2S,4S)-1-[[N-[4-(2-tetrahydropyranyl)oxycarbonylbicyclo[2,2,2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile → (2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 2109490Notes

Reaction equation

HRID 2109490 reaction equation
O1CCCCC1[O:7][C:8]([C:10]12[CH2:17][CH2:16][C:13]([NH:18][CH2:19][C:20]([N:22]3[CH2:26][C@@H:25]([F:27])[CH2:24][C@H:23]3[C:28]#[N:29])=[O:21])([CH2:14][CH2:15]1)[CH2:12][CH2:11]2)=[O:9]>C(O)(=O)C>[C:8]([C:10]12[CH2:17][CH2:16][C:13]([NH:18][CH2:19][C:20]([N:22]3[CH2:26][C@@H:25]([F:27])[CH2:24][C@H:23]3[C:28]#[N:29])=[O:21])([CH2:14][CH2:15]1)[CH2:12][CH2:11]2)([OH:9])=[O:7]

Participants

3

Reactant 1

HCID 59383132(2S,4S)-1-[[N-[4-(2-tetrahydropyranyl)oxycarbonylbicyclo[2,2,2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Product 1

HCID 57634365(2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

(2S,4S)-1-[[N-[4-(2-Tetrahydropyranyl)oxycarbonylbicyclo[2,2,2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (71.6 mg) was dissolved in acetic acid (4 mL) and the solution was stirred at room temperature for 6 hours. Subsequently, the reaction mixture was concentrated under reduced pressure and the residue was suspended in dichloromethane and was collected by filtration. This gave (2S,4S)-1-[[N-(4-carboxybicyclo[2,2,2]oct-1-yl)amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (31.4 mg).

Workup

  1. concentrationSubsequently, the reaction mixture was concentrated under reduced pressure
  2. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-d678ac305bfc4f398bcffc88aaba51bd
Source dataset
uspto-grants-2009_04
Patent number
US07514571B2

Reaction notes

Loading…