Potassium Carbonate → (S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)amino)propanamido)propanoate

HRID 630598Notes

Reaction equation

HRID 630598 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:21][O:22][CH3:23])[C:4]([NH:6][C@@H:7]([CH2:18][O:19][CH3:20])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])=[O:5].[C:24](=[O:27])([O-:26])[O-:25].[K+].[K+]>CN(C=O)C.O>[CH3:20][O:19][CH2:18][C@H:7]([NH:6][C:4](=[O:5])[C@@H:3]([NH:2][CH2:11][C:12]1[O:27][C:24](=[O:26])[O:25][C:13]=1[CH3:14])[CH2:21][O:22][CH3:23])[C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86715352(S)-benzyl 2-((S)-2-amino-3-methoxypropanamido)-3-methoxypropanoate hydrochloride salt

Product 1

HCID 86715351(S)-Benzyl 3-methoxy-2-((S)-3-methoxy-2-(((5-methyl-2-oxo-1,3-dioxol-4-yl)methyl)amino)propanamido)propanoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Referring to FIG. 38, 4-(bromomethyl)-5-methyl-1,3-dioxo-2-one (278 mg. 1.44 mmol) was added to (S)-benzyl 2-((S)-2-amino-3-methoxypropanamido)-3-methoxypropanoate hydrochloride salt (1.0 g, 2.88 mmol) and potassium carbonate (400 mg, 2.88 mmol) in DMF (15 mL) at 0° C. The reaction was stirred at 0° for 2.5 hours and then diluted with water and extracted with EtOAc. The extract was washed with brine, dried (Na2SO4) and evaporated. The residue was purified by Biotage flash column chromatography to give product as a yellow oil. MS for C20H26N2O8 m/z: 423 (M+H)+.

Workup

  1. extractionextracted with EtOAc
  2. washThe extract was washed with brine
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe residue was purified by Biotage flash column chromatography
  6. customto give product as a yellow oil

Sources & evidence

ORD record
ord-73bdba44a519415fb768a2cf4365168d
Source dataset
uspto-grants-2016_04
Patent number
US09315542B2

Reaction notes

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