Sodium Hydroxide → 2-(2-((tert-Butoxycarbonyl)(methyl)amino)-N-methylacetamido)acetic acid

HRID 2079335Notes

Reaction equation

C([O:3][C:4](=[O:20])[CH2:5][N:6]([C:8](=[O:19])[CH2:9][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH3:11])[CH3:7])C.[OH-].[Na+]>CO>[C:15]([O:14][C:12]([N:10]([CH3:11])[CH2:9][C:8]([N:6]([CH2:5][C:4]([OH:20])=[O:3])[CH3:7])=[O:19])=[O:13])([CH3:18])([CH3:17])[CH3:16]

Participants

Conditions

Temperature: 65 °C

Procedure

The ester was taken up in 49 mL of methanol, and to this was added a 1 M NaOH solution (25.1 mL, 25 mmol). The reaction mixture was heated at 65° C. for 3 h. The reaction mixture was cooled, and methanol was removed under reduced pressure. The residue was diluted with 50 mL of water and acidified with glacial acetic acid until the pH was 5. This solution was extracted with EtOAc (50 mL), and the organic layer was separated and dried over Na2SO4, and the solvent was removed under reduced pressure to give {[2-(tert-Butoxycarbonyl-methyl-amino)-acetyl]-methyl-amino}-acetic acid as an oil.

Workup

temperatureThe reaction mixture was cooled
custommethanol was removed under reduced pressure
additionThe residue was diluted with 50 mL of water
extractionThis solution was extracted with EtOAc (50 mL)
customthe organic layer was separated
dry with materialdried over Na2SO4
customthe solvent was removed under reduced pressure

Sources & evidence

ORD record: ord-2833613d65334431b57ae83dee5ae5a1
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07928107B2

Reaction notes

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