Hydrochloric Acid → 1-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetic Acid

HRID 2099260Notes

Reaction equation

HRID 2099260 reaction equation
C([O:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[O:10][C:11]([NH:13][CH2:14][C:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:12])(=O)C.[OH-].[Na+].Cl>CO.O>[OH:4][C@@H:5]1[CH2:9][CH2:8][CH2:7][C@H:6]1[O:10][C:11]([NH:13][CH2:14][C:15]1([CH2:21][C:22]([OH:24])=[O:23])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)=[O:12]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 865905621-{{[2(R)-Acetoxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl-1-Cyclohexane Acetic Acid

Product 1

HCID 865905641-{{{[2(R)-Hydroxycyclopent-1(R)-yl]oxy}carbonyl}aminomethyl}-1-Cyclohexane Acetic AcidYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of compound (48) (2.0 g, 5.9 mmol) in methanol (25 mL) was added a solution of NaOH (0.8 g, 20 mmol) in 20 mL of water. The reaction mixture was stirred at room temperature for 2 h (monitored by TLC). The reaction mixture was acidified to about pH 5.0 using 0.1 N HCl and then extracted using ethyl acetate (2×50 mL). The combined extracts were washed with brine (40 mL), dried over MgSO4 and concentrated in vacuo. The crude product was purified using flash chromatography on silica gel using hexane/ethyl acetate (1:1) as eluant to provide 1.3 g (75%) of compound (49) as a colorless oil. 1H NMR (400 MHz, CDCl3): δ1.36-1.78 (14H, m); 1.99-2.12 (2H, m); 2.34 (2H, s); 3.23 (2H, d, J=6.4 Hz); 4.09 (1H, m); 5.26 (1H, t, J=6.4 Hz); 5.89 (1H, m). MS (ESI): m/z=298.23 (M−H−).

Workup

  1. extractionextracted
  2. washThe combined extracts were washed with brine (40 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified

Sources & evidence

ORD record
ord-70164f8b074740e89fcf9610ebb0f850
Source dataset
uspto-grants-2009_08
Patent number
US07569576B2

Reaction notes

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