Water → Methyl (2S)-2-((tert-butoxycarbonyl)amino)-3-(2-oxopyrrolidin-3-yl)propanoate

HRID 58827Notes

Reaction equation

HRID 58827 reaction equation
[NH2:1][CH2:2][CH2:3][CH:4]([CH2:9][C@H:10]([NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:11]([O:13][CH3:14])=[O:12])[C:5](OC)=[O:6].CCN(CC)CC.O>C1COCC1>[C:19]([O:18][C:16]([NH:15][C@@H:10]([CH2:9][CH:4]1[CH2:3][CH2:2][NH:1][C:5]1=[O:6])[C:11]([O:13][CH3:14])=[O:12])=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 962WaterHCID 8471TriethylamineHCID 117608156HCID 117608156, compound

Product 1

HCID 89483741Methyl (2S)-2-((tert-butoxycarbonyl)amino)-3-(2-oxopyrrolidin-3-yl)propanoateYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of (4S)-dimethyl 2-(2-aminoethyl)-4-((tert-butoxycarbonyl)amino)pentanedioate (crude) in THF (20 mL) was added Et3N (20 mL). The reaction mixture was stirred at 60° C. overnight and then cooled to ambient temperature. Water (50 mL) was added and the resulting mixture was extracted with methylene chloride (100 mL×2). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash column chromatography on silica gel (heptanes/EtOAc=1:1) to afford (2S)-methyl 2-((tert-butoxycarbonyl)amino)-3-(2-oxopyrrolidin-3-yl)propanoate (5.5 g, 60% yield over two steps) as a light brown oil.

Workup

  1. temperaturecooled to ambient temperature
  2. extractionthe resulting mixture was extracted with methylene chloride (100 mL×2)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash column chromatography on silica gel (heptanes/EtOAc=1:1)

Sources & evidence

ORD record
ord-b7c1ff429df04e1dbe23c03cf0f59d86
Source dataset
uspto-grants-2016_09
Patent number
US09434761B2

Reaction notes

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