Sodium Acetate → Benzyl 1-{{{[2-Oxo-cyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetate

HRID 1795205Notes

Reaction equation

HRID 1795205 reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]([NH:10][CH2:11][C:12]1([CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:9].[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1.CC([O-])=O.[Na+]>ClCCl>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][C@H:3]1[O:7][C:8]([NH:10][CH2:11][C:12]1([CH2:18][C:19]([O:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)=[O:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)=[O:9]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 86590565Benzyl 1-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane AcetateHCID 178418287HCID 178418287, compound

Product 1

HCID 86590566Benzyl 1-{{{[2-Oxo-cyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of compound (50) (0.50 g, 1.3 mmol) in dichloromethane (15 mL) was added pyridinium chlorochromate (0.55 g, 2.6 mmol) followed by NaOAc (0.21 g, 2.57 mmol) at room temperature. The resulting reaction was stirred overnight at room temperature (monitored by LC/MS), then filtered. The solid was washed with dichloromethane (2×25 mL) and the combined filtrates were washed with water (2×25 mL), dried over MgSO4 and concentrated in vacuo to provide compound 51 which was used in the next step without further purification. MS (ESI): m/z=388.38 (M+H+).

Workup

  1. customThe resulting reaction
  2. filtrationfiltered
  3. washThe solid was washed with dichloromethane (2×25 mL)
  4. washthe combined filtrates were washed with water (2×25 mL)
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d79d0b731a0c45eca91863bbdb0d317f
Source dataset
uspto-grants-2006_04
Patent number
US07026351B2

Reaction notes

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