Acetic Acid → HCID 58981716, compound

HRID 1182280Notes

Reaction equation

HRID 1182280 reaction equation
[CH3:1][C@H:2]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH:3]=[O:4].[C-:13]#[N:14].[K+].C(O)(=O)C>CO>[NH2:14][CH2:13][C@H:3]([OH:4])[C@@H:2]([NH:5][C:6](=[O:12])[O:7][C:8]([CH3:11])([CH3:10])[CH3:9])[CH3:1]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 9032Potassium CyanideHCID 7015728tert-butyl N-((2S)-1-oxopropan-2-yl)carbamate

Product 1

HCID 58981716HCID 58981716, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5.25 g (30.4 mmol) of tert-butyl (1S)-1-methyl-2-oxoethylcarbamate in 30 mL of methanol at 0° C. was added 2.18 g (33.4 mmol) of potassium cyanide, followed by 1.74 mL (33.4 mmol) of acetic acid. The reaction mixture was warmed to room temperature, left stirring for 16 h, and then filtered and concentrated under vacuum. The residue was dissolved in 80 mL of acetic acid, and 0.8 g of platinum oxide on carbon was added. The reaction mixture was then stirred under 40 psi of hydrogen for 4 h. The catalyst was filtered off over celite, and the filtrate was washed with methanol and concentrated to afford 3.06 g (49%) of tert-butyl (1S,2S)-3-amino-2-hydroxy-1-methylpropylcarbamate & tert-butyl (1S,2R)-3-amino-2-hydroxy-1-methylpropylcarbamate. 1H-NMR (300 MHz, DMSO-d6): δ 6.74, 6.59 (d, J=8 Hz, 1H), 3.61–3.38 (m, 3H), 2.80 (m, 1H), 2.51 (m, 2H), 1.45 (br s, 1H), 1.38 (s, 9H), 0.97 (m, 3H). GC-MS m/z 205 (M+H).

Workup

  1. waitleft
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in 80 mL of acetic acid
  5. addition0.8 g of platinum oxide on carbon was added
  6. stirringThe reaction mixture was then stirred under 40 psi of hydrogen for 4 h
  7. filtrationThe catalyst was filtered off over celite
  8. washthe filtrate was washed with methanol
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6834bad752bc43b693cea503ef73af06
Source dataset
uspto-grants-2007_10
Patent number
US07288541B2

Reaction notes

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