Methyl (2S)-2-oxiranecarboxylate → HCID 66813352, compound

HRID 1098276Notes

Reaction equation

HRID 1098276 reaction equation
[Si:1]([O:18][CH2:19][CH:20]1[CH2:23][NH:22][CH2:21]1)([C:14]([CH3:17])([CH3:16])[CH3:15])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[O:24]1[CH2:26][C@H:25]1[C:27]([O:29][CH3:30])=[O:28]>C(#N)C>[Si:1]([O:18][CH2:19][CH:20]1[CH2:23][N:22]([CH2:26][C@H:25]([OH:24])[C:27]([O:29][CH3:30])=[O:28])[CH2:21]1)([C:14]([CH3:17])([CH3:15])[CH3:16])([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

4

Reactant 2

HCID 10942355Methyl (2S)-2-oxiranecarboxylateHCID 57438675HCID 57438675, compound

Product 1

HCID 66813352HCID 66813352, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
85 °C

Procedure

3-((tert-Butyldiphenylsilyloxy)methyl)azetidine (Intermediate BG3) (7.461 g, 22.92 mmol) and (S)-methyl oxirane-2-carboxylate (2.340 g, 22.92 mmol) were dissolved in acetonitrile (50 mL) and heated to 85° C. for 90 minutes. The resulting mixture was cooled and evaporated to dryness. The crude product was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM to afford the product (9.6 g, 56%).

Workup

  1. temperatureThe resulting mixture was cooled
  2. customevaporated to dryness
  3. customThe crude product was purified by flash silica chromatography, elution gradient 0 to 5% MeOH in DCM

Sources & evidence

ORD record
ord-4a8e48c7405940adb9f5ee0da66c2e39
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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