Sodium Hydroxide → HCID 23853315, compound

HRID 1455248Notes

Reaction equation

HRID 1455248 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH2:15][NH:14]1)=[O:12])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH2:18]([O:20][C:21](=[O:26])[CH2:22][C:23](Cl)=[O:24])[CH3:19]>C(Cl)Cl>[CH2:3]([O:10][C:11]([N:13]1[CH2:17][CH2:16][CH2:15][N:14]1[C:23](=[O:24])[CH2:22][C:21]([O:20][CH2:18][CH3:19])=[O:26])=[O:12])[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 11564702Benzyl Pyrazolidine-1-carboxylate

Product 1

HCID 23853315HCID 23853315, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of sodium hydroxide (93.0 mL of 1N solution, 93.0 mmol) is added CH2Cl2 (280 mL) followed by pyrazolidine-1-carboxylic acid benzyl ester (15.0 g, 61.8 mmol) and then ethyl-3-chloro-3-oxopropionate (11.1 mL, 86.5 mmol). After stirring the biphasic mixture vigorously for 3 hours at room temperature, the mixture is quenched by pouring into aqueous saturated NH4Cl. The organic phase is dried (MgSO4), filtered and concentrated in vacuo. The crude residue is purified over silica (10% EtOAc/hexanes) to afford 15.5 g (78% yield) of the desired product. 1H NMR (300 MHz, CDCl3) δ 7.38 (s, 5H), 5.23 (dd, J=11.8, 8.4 Hz, 2H), 4.19-4.07 (m, 4H), 3.65 (d, J=15.9 Hz, 1H), 3.31 (d, J=15.9 Hz, 1H), 3.20-3.15 (m, 2H), 2.20-2.04 (m, 2H), 1.26 (t, J=7.2 Hz, 3H); ESI+ MS: m/z (rel intensity) 321.0 (100, M++H).

Workup

  1. customthe mixture is quenched
  2. additionby pouring into aqueous saturated NH4Cl
  3. dry with materialThe organic phase is dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue is purified over silica (10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d7ddda88bc8e45228bdadb196882a87d
Source dataset
uspto-grants-2009_01
Patent number
US07482356B2

Reaction notes

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