Triethylamine → HCID 69352548, compound

HRID 2303370Notes

Reaction equation

HRID 2303370 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([C:23]([OH:25])=O)[CH:20]([CH3:22])[CH3:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=O.[CH2:32]([O:34][C:35](=[O:45])[CH2:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:33].C(N(CC)CC)C>ClCCl.CN(C=O)C>[CH2:32]([O:34][C:35](=[O:45])[CH2:36][N:37]([C:23](=[O:25])[C@H:19]([CH:20]([CH3:22])[CH3:21])[NH:18][C:16]([O:15][CH2:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:17])[CH2:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH3:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 80908N-Benzylglycine ethyl esterHCID 688217FMOC-L-valine

Product 1

HCID 69352548HCID 69352548, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

N-(9-Fluorenylmethoxycarbonyl)-L-valine (1.0 g) was dissolved in a mixed solvent of dichloromethane (10 mL) and DMF (0.1 mL), and to the solution oxalyl chloride (374 mg) was added dropwise at 0° C. The mixture was stirred for 30 minutes and added dropwise into a solution of N-(benzyl)glycine ethyl ester (587 mg) and triethylamine (477 mg) in dichloromethane (10 mL) at 0° C. The resultant mixture was stirred at room temperature for 2 hours, and the reaction mixture was concentrated under reduced pressure. Ethyl acetate was added to the residue, and the mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1) to obtain the title compound.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionEthyl acetate was added to the residue
  3. washthe mixture was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-10baf60e5cea4d038833ba93ef73636d
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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