Water → Methyl-(s)-1-[(s)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl-amino]-1-oxo-3-phenylpropan-2-ylcarbamate

HRID 925284Notes

Reaction equation

HRID 925284 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]([C@@H:8]([NH:19][C:20](=[O:37])[C@@H:21]([NH:29][C:30](=[O:36])[O:31][C:32](C)(C)C)[CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)[S:6][CH:7]=1)[CH3:2].ClC(OC)=O.O>Cl.O1CCOCC1>[CH3:32][O:31][C:30](=[O:36])[NH:29][C@@H:21]([CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[C:20]([NH:19][C@H:8]([C:5]1[S:6][CH:7]=[C:3]([CH2:1][CH3:2])[N:4]=1)[CH2:9][C:10]1[CH:11]=[CH:12][C:13]([N+:16]([O-:18])=[O:17])=[CH:14][CH:15]=1)=[O:37]

Participants

6

Reactant 3

HCID 962WaterHCID 6586Methyl chloroformateHCID 57943172Tert-butyl (5)-1-[(5)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino]-1-oxo-3-phenylpropan-2-ylcarbamate

Product 1

HCID 57943180Methyl-(s)-1-[(s)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl-amino]-1-oxo-3-phenylpropan-2-ylcarbamate

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

tert-butyl (S)-1-[(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethylamino]-1-oxo-3-phenylpropan-2-ylcarbamate, 8, (0.460 mg, 0.881 mmol) is dissolved in a solution of 4M hydrogen chloride in 1,4-dioxane (4 mL). The reaction mixture is stirred 1 hour, and the solvent is removed under reduced pressure. The resulting crude amine is dissolved in CHCl3 (8 mL) and pyridine (1 mL) is added. The temperature is cooled to 0° C. and methyl chloroformate (0.083 g, 0.881 mmol) is added dropwise. The reaction mixture is allowed to warm to room temperature and stirred for 2 days. Water is added, the solution stirred for 15 minutes and then extracted several times with CHCl3. The combined organic layers are washed with 1N HCl, 5% NaHCO3, and brine, dried over Na2SO4, and filtered. The solvent is removed in vacuo to afford 0.297 g of the desired product.

Workup

  1. customthe solvent is removed under reduced pressure
  2. dissolutionThe resulting crude amine is dissolved in CHCl3 (8 mL)
  3. additionpyridine (1 mL) is added
  4. temperatureto warm to room temperature
  5. stirringstirred for 2 days
  6. stirringthe solution stirred for 15 minutes
  7. extractionextracted several times with CHCl3
  8. washThe combined organic layers are washed with 1N HCl, 5% NaHCO3, and brine
  9. dry with materialdried over Na2SO4
  10. filtrationfiltered
  11. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-395fb9e00c284c859b0f01cacff91687
Source dataset
uspto-grants-2016_03
Patent number
US09284285B2

Reaction notes

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