Methanol → (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate

HRID 451867Notes

Reaction equation

HRID 451867 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].S(C)C.CO>C1COCC1>[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:10][OH:11])[CH2:13][CH2:14][C:15]([O:17][CH3:18])=[O:16])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 887MethanolHCID 1068Dimethyl SulfideHCID 7018756(S)-2-((tert-butoxycarbonyl)amino)-5-methoxy-5-oxopentanoic acid

Product 1

HCID 11107667(S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoateYield 49%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution (S)-2-(tert-butoxycarbonylamino)-5-methoxy-5-oxopentanoic acid (26.1 g, 0.1 mol) in THF (500 mL), BH3.Me2S (80 mL, 0.8 mmol) was added dropwise at −78° C., then stirred at rt for 3 hrs. The reaction was stopped by careful addition of methanol. After evaporation and three distillations of methanol, the residue was dissolved in EtOAc, washed with 1 M NaHCO3, and brine. (S)-methyl 4-(tert-butoxycarbonylamino)-5-hydroxypentanoate (12 g, yield 49%) was obtained as an oil that was used in the next step without further purification.

Workup

  1. customAfter evaporation and three distillations of methanol
  2. dissolutionthe residue was dissolved in EtOAc
  3. washwashed with 1 M NaHCO3, and brine

Sources & evidence

ORD record
ord-7c10b6e8df794ab78bcc16b9d584b0d9
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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