Methanol → HCID 68863165, compound

HRID 1985802Notes

Reaction equation

HRID 1985802 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][S:14]([CH2:17][C:18]1[CH:23]=[N:22][CH:21]=[CH:20][N:19]=1)(=[O:16])=[O:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24]O>C1(C)C=CC=CC=1.[Si](C=[N+]=[N-])(C)(C)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][S:14]([CH2:17][C:18]1[CH:23]=[N:22][CH:21]=[CH:20][N:19]=1)(=[O:15])=[O:16])[C:10]([O:12][CH3:24])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 68864051HCID 68864051, compound

Product 1

HCID 68863165HCID 68863165, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 167693TrimethylsilyldiazomethaneSolvent

Procedure

(R)-tert-Butoxycarbonylamino-3-(pyrazin-2-ylmethanesulfonyl)propionic acid (1.42 g, 4.53 mmol) was dissolved in mixture of MeOH (10 mL) and toluene (33 mL) and Me3SiCHN2 (2.0 M solution in hexanes, 3.06 ml) was added dropwise over 10 min. After stirring the reaction mixture overnight, the solvent was removed and the resulting residure was purified by flash chromatography with EtOAc/hexanes as eluent to afford methyl 2(R)-tert-butoxycarbonylamino-3-(pyrazin-2-ylmethanesulfonyl)propionate (0.755 g).

Workup

  1. additionwas added dropwise over 10 min
  2. customthe solvent was removed
  3. customthe resulting residure was purified by flash chromatography with EtOAc/hexanes as eluent

Sources & evidence

ORD record
ord-433543194a4d4f5e8516e09e8b08f2d1
Source dataset
uspto-grants-2009_06
Patent number
US07547701B2

Reaction notes

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