HCID 66874102, compound → HCID 59180220, compound

HRID 601955Notes

Reaction equation

HRID 601955 reaction equation
[F:1][C:2]1([F:16])[CH2:13][C:5]2[NH:6][C:7]([C:9]([O:11]C)=[O:10])=[CH:8][C:4]=2[CH:3]1[O:14][CH3:15]>CCOC(C)=O>[F:16][C:2]1([F:1])[CH2:13][C:5]2[NH:6][C:7]([C:9]([OH:11])=[O:10])=[CH:8][C:4]=2[CH:3]1[O:14][CH3:15]

Participants

3

Reactant 1

HCID 66874102HCID 66874102, compound

Product 1

HCID 59180220HCID 59180220, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
34.5 °C

Procedure

A magnetically-stirred solution/suspension of methyl 5,5-difluoro-4-methoxy-1,4,5,6-tetrahydrocyclopenta[b]pyrrole-2-carboxylate, (17.40 mg, 0.075 mmol) in pH=7 buffer solution, was treated with pig-liver esterase (PLE) (64.44 mg, 100 U/mg), and warmed at 32-37° C. for a period of 18 h after conversion to product appeared to stop. The suspension was diluted with EtOAc (20 mL) and dried onto Celite. The crude was then purified by silica gel chromatography (twice). 7.9 mg. 1H NMR (400 MHz, ACETONE-d6) δ ppm 3.17-3.41 (m, 2H), 3.43 (s, 3H), 4.60 (d, J=13.28 Hz, 1H), 6.81 (s, 1H), 10.93 (br. s., 1H); 19F NMR (400 MHz, ACETONE-d6) δ ppm −105.48 (d, J=0.63 Hz, 1F), −93.65 (d, J=0.65 Hz, 1F); LCMS-MS (ESI−) 216.2 (M-1).

Workup

  1. additionwas treated with pig-liver esterase (PLE) (64.44 mg, 100 U/mg)
  2. customdried onto Celite
  3. customThe crude was then purified by silica gel chromatography (twice)

Sources & evidence

ORD record
ord-4908b8305499417cb6710e0d623461df
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

Loading…