Triethylamine → HCID 53979190, compound

HRID 1647091Notes

Reaction equation

HRID 1647091 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:13]([OH:15])=O)[CH:10]([CH3:12])[CH3:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC(C)C)=O.[CH2:31]([O:38][C:39](=[O:51])[CH2:40][NH:41][CH:42]1[CH2:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43]1)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>C(Cl)Cl>[CH2:31]([O:38][C:39](=[O:51])[CH2:40][N:41]([C:13](=[O:15])[C@H:9]([CH:10]([CH3:11])[CH3:12])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH:42]1[CH2:50][C:49]2[C:44](=[CH:45][CH:46]=[CH:47][CH:48]=2)[CH2:43]1)[C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 83693Boc-L-ValineHCID 13089232HCID 13089232, compound

Product 1

HCID 53979190HCID 53979190, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of N-(tert-butoxycarbony1)-L-valine (4.35 g) and triethylamine (2.13 g) in dry CH2Cl2 (40 ml) was added isobutyl chloroformate (2.87 g) at -20° C. After being stirred at same temperature for 30 minutes, a solution of N-(2-indanyl)glycine benzyl ester (5.37 g) in dry CH2Cl2 (20 ml) was added at -20° C. The reaction mixture was stirred at -10° C. for one hour then at room temperature for 4 hours. After the reaction mixture was evaporated under reduced pressure, the residue was dissolved in ethyl acetate (100 ml) and washed with saturated aqueous sodium bicarbonate (100 ml×2). The organic layer was dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified with silica gel (50 g) column chromatography (CHCl3:AcOEt=10:1) to give N-(tert-butoxycarbonyl)-L-valyl-N-(2-indanyl)glycine benzyl ester (2.20 g) as an oil.

Workup

  1. stirringThe reaction mixture was stirred at -10° C. for one hour
  2. waitat room temperature for 4 hours
  3. customAfter the reaction mixture was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  5. washwashed with saturated aqueous sodium bicarbonate (100 ml×2)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was purified with silica gel (50 g) column chromatography (CHCl3:AcOEt=10:1)

Sources & evidence

ORD record
ord-4e182b9e1d8c4c478f3845c803327ecd
Source dataset
uspto-grants-1995_07
Patent number
US05430025

Reaction notes

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