Sodium Hydroxide → 2-(2-Trityloxycarbamoyl-ethyl)-succinic acid 4-tert-butyl ester

HRID 902929Notes

Reaction equation

HRID 902929 reaction equation
C[O:2][C:3](=[O:38])[CH:4]([CH2:13][CH2:14][C:15](=[O:37])[NH:16][O:17][C:18]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].[OH-].[Na+]>CO.O>[C:9]([O:8][C:6](=[O:7])[CH2:5][CH:4]([CH2:13][CH2:14][C:15](=[O:37])[NH:16][O:17][C:18]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)([C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:3]([OH:38])=[O:2])([CH3:12])([CH3:10])[CH3:11]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131725937HCID 131725937, compound

Product 1

HCID 877349892-(2-Trityloxycarbamoyl-ethyl)-succinic acid 4-tert-butyl ester

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of the compound of example 65 (2.27 g, 4.39 mmol) in a mixture of methanol/water (4:1, 50 mL) was added a solution of sodium hydroxide (1N, 9 mL). The resulting mixture was stirred for 24 h at room temperature. The solvent was evaporated and the residue was partitioned between water and ether. The alkaline phase acidified using HCl (6N) and extracted with ethyl acetate followed by drying over sodium sulfate, filtration and evaporation. The product was converted to an off-white foam under high vacuum. 1H-NMR(CDCl3, 400 MHz: 1.42(s, 9H); 1.59(m, 3H); 1.88-2.54(m, 4H); 7.33(m, 15H); 7.46(s, broad, 1H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was partitioned between water and ether
  3. extractionextracted with ethyl acetate
  4. dry with materialby drying over sodium sulfate, filtration and evaporation

Sources & evidence

ORD record
ord-8de34138c0a44a3d942235bafa23c9c2
Source dataset
uspto-grants-2008_04
Patent number
US07365091B2

Reaction notes

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