Sodium Bicarbonate → HCID 86607907, compound

HRID 736812Notes

Reaction equation

HRID 736812 reaction equation
[NH2:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@:3]1([F:11])[C:7]([O:9][CH3:10])=[O:8].[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26](Cl)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH2:12]([O:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([NH:1][C@@H:2]2[CH2:6][CH2:5][CH2:4][C@:3]2([F:11])[C:7]([O:9][CH3:10])=[O:8])(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 47383854-(Benzyloxy)benzene-1-sulfonyl chlorideHCID 86607908HCID 86607908, compound

Product 1

HCID 86607907HCID 86607907, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl (1R,2R)-2-amino-1-fluorocyclopentanecarboxylate (0.47 g, 2.4 mmol, 1 eq) in CH2Cl2 (10 mL) was added 4-benzyloxy-benzenesulfonyl chloride followed by saturated sodium bicarbonate (10 mL). The reaction was stirred overnight, and then taken up in ethyl acetate. The organics were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified using silica chromatography eluting with 30% ethyl acetate/hexanes to afford methyl (1R,2R)-2-({[4-(benzyloxy)phenyl]sulfonyl}amino)-1-fluorocyclopentanecarboxylate as an off white solid (0.575 g, 60%). MS: 408.1 (M+H)+.

Workup

  1. washThe organics were washed with brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified
  6. washeluting with 30% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-78d92b049822472d9d3f9e511816b83d
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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