Trimethylsilyldiazomethane → HCID 86710402, compound

HRID 1398414Notes

Reaction equation

HRID 1398414 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]([CH3:16])=[CH2:15])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Si](C=[N+]=[N-])(C)(C)[CH3:18]>O1CCCC1>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][C:14]([CH3:16])=[CH2:15])[C:10]([O:12][CH3:18])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 2755921(S)-2-(Boc-amino)-4-methyl-4-pentenoic acid

Product 1

HCID 86710402HCID 86710402, compoundYield 99.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (S)-2-((tert-butoxycarbonyl)amino)-4-methylpent-4-enoic acid (550 mg, 2.399 mmol) in tetrahydrofuran (11 mL) at 0° C., was added TMS-diazomethane (4.80 mL, 4.80 mmol) dropwise over 5 min. The reaction mixture was then stirred at 0° C. for 15 min. After gradually warmed to room temperature, the mixture was stirred for 16 h. The reaction mixture was evaporated to dryness to afford (S)-methyl 2-((tert-butoxycarbonyl)amino)-4-methylpent-4-enoate (580 mg, 2.386 mmol, 99% crude yield) as a dark yellow oil which was taken to the next step without purification. 1H NMR (400 MHz, CDCl3): δ ppm 4.91 (s, 1H), 4.85 (s, 1H), 4.75 (s, 1H), 4.38 (q, J=16.00 Hz, 1H), 3.73 (s, 3H), 2.33-2.53 (m, 2H), 1.71 (s, 3H), 1.43 (s, 9H).

Workup

  1. temperatureAfter gradually warmed to room temperature
  2. stirringthe mixture was stirred for 16 h
  3. customThe reaction mixture was evaporated to dryness

Sources & evidence

ORD record
ord-c3ce6825c9dc4d47ab56e1aa67fd1400
Source dataset
uspto-grants-2014_12
Patent number
US08901305B2

Reaction notes

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