HCID 86607907, compound → HCID 86607909, compound

HRID 736813Notes

Reaction equation

HRID 736813 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([S:15]([NH:18][C@@H:19]2[CH2:23][CH2:22][CH2:21][C@:20]2([F:28])[C:24]([O:26][CH3:27])=[O:25])(=[O:17])=[O:16])=[CH:11][CH:10]=1)C1C=CC=CC=1>CCOC(C)=O.C(Cl)Cl.CO.[Pd]>[F:28][C@:20]1([C:24]([O:26][CH3:27])=[O:25])[CH2:21][CH2:22][CH2:23][C@H:19]1[NH:18][S:15]([C:12]1[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=1)(=[O:16])=[O:17]

Participants

4

Reactant 1

HCID 86607907HCID 86607907, compound

Product 1

HCID 86607909HCID 86607909, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21901258Dichloromethane ethyl acetate methanolSolvent

Procedure

To a solution of methyl (1R,2R)-2-({[4-(benzyloxy)phenyl]sulfonyl}amino)-1-fluorocyclopentanecarboxylate in EtOAc/CH2Cl2/MeOH (5 mL/2 mL/10 mL) was added 10% Pd/C (0.14 g). The reaction vessel was purged with nitrogen followed by hydrogen. The reaction was stirred for 1 h under 1 atmosphere of hydrogen, and then filtered through celite and concentrated to afford methyl (1R,2R)-1-fluoro-2-{[(4-hydroxyphenyl)sulfonyl]amino}cyclopentanecarboxylate as an amorphous solid (0.433 g, 97%). MS: 318.1 (M+H)+.

Workup

  1. customThe reaction vessel was purged with nitrogen
  2. filtrationfiltered through celite
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f41df6c0668e4332a51076ddff73226f
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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