Triethylamine → HCID 118242169, compound

HRID 1526781Notes

Reaction equation

HRID 1526781 reaction equation
Cl.[NH2:2][C@H:3]([C:10]1[CH:15]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:13]=[C:12]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH:11]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:24][C:25]([O:28][C:29]([NH:31][CH2:32][C:33](ON1C(=O)CCC1=O)=[O:34])=[O:30])([CH3:27])[CH3:26].C(N(CC)CC)C>CN(C=O)C>[C:25]([O:28][C:29]([NH:31][CH2:32][C:33]([NH:2][C@H:3]([C:10]1[CH:11]=[C:12]([C:20]([CH3:22])([CH3:21])[CH3:23])[CH:13]=[C:14]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:15]=1)[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:34])=[O:30])([CH3:27])([CH3:26])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76926N-(tert-Butyloxycarbonyl)glycine N-hydroxysuccinimide esterHCID 131733184HCID 131733184, compound

Product 1

HCID 118242169HCID 118242169, compoundYield 107%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of a mixture of (S)-ethyl 3-amino-3-(3,5-di-tert-butylphenyl)propionate hydrochloride (112.0 mg, 0.33 mmol) and Boc-Gly-Osu (95.0 mg, 0.35 mmol) in anhydrous DMF was added triethylamine (62 μL, 0.45 mmol) and the reaction mixture was stirred at room temperature under nitrogen atmosphere overnight to give a colorless solution. The solvent was evaporated in-vacuo and the residue was partitioned between ethyl acetate (25 mL), water (25 mL) and saturated NaHCO3 solution (10 mL). The organic layer was removed, washed with water (1×10 mL), dried over anhydrous Na2SO4, filtered and evaporated in vacuo to afford a cream foamy solid (163.4 mg). LC-MS analysis of the solid shows the desired product's mass: m/z 463 (M+H) and m/.z 485 (M+Na); Calcd for C26H42N2O5: 462.62. The above product will be used as such for the Boc-deprotection. (step #5).

Workup

  1. customto give a colorless solution
  2. customThe solvent was evaporated in-vacuo
  3. customthe residue was partitioned between ethyl acetate (25 mL), water (25 mL) and saturated NaHCO3 solution (10 mL)
  4. customThe organic layer was removed
  5. washwashed with water (1×10 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-fa9dd198636143a1bf18db40590cf980
Source dataset
uspto-grants-2015_07
Patent number
US09085606B2

Reaction notes

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