Acetic Acid → [2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-carbamic Acid Tert-Butyl Ester

HRID 1453333Notes

Reaction equation

HRID 1453333 reaction equation
C[O:2][C:3](=[O:25])[CH2:4][C:5](=[O:24])[CH2:6][C:7]([CH:19]1[CH2:23][CH2:22][CH2:21][CH2:20]1)(O)[CH2:8][CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12].[OH-].[Na+].C(O)(=O)C>CO>[C:14]([O:13][C:11](=[O:12])[NH:10][CH2:9][CH2:8][C:7]1([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23]2)[CH2:6][C:5](=[O:24])[CH2:4][C:3](=[O:2])[O:25]1)([CH3:15])([CH3:16])[CH3:17]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 587625517-tert-Butoxycarbonylamino-5-cyclopentyl-5-hydroxy-3-oxo-heptanoic Acid Methyl Ester

Product 1

HCID 58762283[2-(2-Cyclopentyl-4,6-dioxo-tetrahydro-pyran-2-yl)-ethyl]-carbamic Acid Tert-Butyl EsterYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 7-tert-butoxycarbonylamino-5-cyclopentyl-5-hydroxy-3-oxo-heptanoic acid methyl ester (1.36 g, 3.8 mmol) from Step 3 above dissolved in MeOH (50 mL) was added a NaOH solution (2.8 M, 2.7 mL, 7.6 mmol). The reaction was stirred at room temperature for 18 hours. The reaction was then quenched with acetic acid (0.44 mL, 7.7 mmol) and concentrated by rotary evaporation to an oil. The oil was dissolved in CH2Cl2 and washed with water. The organic layer was separated, and dried over Na2SO4. The solids were removed by filtration, and the liquid was concentrated to yield the product (1.061 g, 86% yield). MS (ESI): 324 (M−H).

Workup

  1. concentrationconcentrated by rotary evaporation to an oil
  2. dissolutionThe oil was dissolved in CH2Cl2
  3. washwashed with water
  4. customThe organic layer was separated
  5. dry with materialdried over Na2SO4
  6. customThe solids were removed by filtration
  7. concentrationthe liquid was concentrated

Sources & evidence

ORD record
ord-ba59d3a3ca524bb48b74dedadd2f6d92
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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