Triethylamine → Boc-L-Valyl-N-Mehtyl-L-Alanyl-L-Alanine Benzyl Ester

HRID 2072756Notes

Reaction equation

HRID 2072756 reaction equation
[CH2:1]([O:8][C:9](=[O:19])[C@H:10]([CH3:18])[NH:11][C:12](=[O:17])[C@H:13]([CH3:16])[NH:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([NH:27][C@H:28]([C:32](O)=[O:33])[CH:29]([CH3:31])[CH3:30])([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C(N(CC)CC)C.C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1>ClCCl>[CH2:1]([O:8][C:9](=[O:19])[C@H:10]([CH3:18])[NH:11][C:12](=[O:17])[C@H:13]([CH3:16])[N:14]([C:32](=[O:33])[C@H:28]([CH:29]([CH3:30])[CH3:31])[NH:27][C:20]([O:22][C:23]([CH3:24])([CH3:25])[CH3:26])=[O:21])[CH3:15])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 83693Boc-L-ValineHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 14673104N-Methyl-L-Alanyl-L-Alanine benzyl Ester

Product 1

HCID 14673106Boc-L-Valyl-N-Mehtyl-L-Alanyl-L-Alanine Benzyl Ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 10.75 g (0.0407 mole) of N-methyl-L-alanyl-L-alanine benzyl ester and 9.73 g (0.0448 mole) of Boc-L-valine in 200 ml of dry dichloromethane was stirred and cooled at -10° C. as 9.97 g (0.0986 mole) of triethylamine was added. After stirring for 15 minutes, 12.55 g (0.0493 mole) of BOP-Cl was added and the reaction was stirred at -5° C. for 22 hours. The reaction was diluted with 100 ml of dichloromethane, washed with 100 ml of 10% potassium bisulfate, washed with 2×75 ml of saturated sodium bicarbonate solution, dried over magnesium sulfate, concentrated, and chromatographed on silica gel using 1:1 ether/hexane as the eluent. The product weighed 17.1 g (91% of theory). Its 200 MHz NMR spectrum in chloroform-d was consistent with the proposed structure.

Workup

  1. additionwas added
  2. stirringAfter stirring for 15 minutes
  3. stirringthe reaction was stirred at -5° C. for 22 hours
  4. washwashed with 100 ml of 10% potassium bisulfate
  5. washwashed with 2×75 ml of saturated sodium bicarbonate solution
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated
  8. customchromatographed on silica gel using 1:1 ether/hexane as the eluent

Sources & evidence

ORD record
ord-6f95f358a42d448dba727778734b73fa
Source dataset
uspto-grants-1990_04
Patent number
US04914188

Reaction notes

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