Water → Z-N-Me-Val-N-Me-Tyr(3-tBu)-NHOMe

HRID 1988243Notes

Reaction equation

HRID 1988243 reaction equation
[NH:1]([CH3:20])[C@H:2]([C:15]([NH:17][O:18][CH3:19])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:5]=1.[C:21]([N:31]([CH3:39])[C@H:32]([C:36]([OH:38])=O)[CH:33]([CH3:35])[CH3:34])([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)=[O:22].O>C1COCC1>[C:21]([N:31]([CH3:39])[C@H:32]([C:36]([N:1]([CH3:20])[C@H:2]([C:15]([NH:17][O:18][CH3:19])=[O:16])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[C:6]([C:11]([CH3:14])([CH3:12])[CH3:13])[CH:5]=1)=[O:38])[CH:33]([CH3:34])[CH3:35])([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)=[O:22]

Participants

5

Reactant 3

HCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131727512N-Me-Tyr(3-tBu)-NHOMe

Product 1

HCID 131727511Z-N-Me-Val-N-Me-Tyr(3-tBu)-NHOMeYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-Me-Tyr(3-tBu)-NHOMe (1.24 g, 4.42 mmol), Z-N-Me-Val-OH (1.76 g, 6.63 mmol) and CMPI (1.7 g, 6.63 mmol) in THF (30 ml), TEA (1.23 ml, 8.84 mmol) was added and stirred overnight. The mixture was mixed with water, extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and evaporated to remove the solvent under reduced pressure. The thus obtained residue was subjected to silica gel column chromatography (developing solvent: ethyl acetate:n-hexane=1:1) to give the titled compound (1.32 g, 57%).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated
  4. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-55e28cdae8f74286adfb63649179af03
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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