Water → Z-N-Me-Val-Tyr(3-tBu)-NH2

HRID 1988270Notes

Reaction equation

HRID 1988270 reaction equation
[NH2:1][C@H:2]([C:15]([NH2:17])=[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:18]([N:28]([CH3:36])[C@H:29]([C:33](O)=[O:34])[CH:30]([CH3:32])[CH3:31])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19].O>C1COCC1>[C:18]([N:28]([CH3:36])[C@H:29]([C:33]([NH:1][C@H:2]([C:15]([NH2:17])=[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:34])[CH:30]([CH3:32])[CH3:31])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19]

Participants

5

Reactant 3

HCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131722727Tyr(3-tBu)-NH2

Product 1

HCID 131722729Z-N-Me-Val-Tyr(3-tBu)-NH2Yield 83.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the thus obtained Tyr(3-tBu)-NH2 (1 g, 4.23 mmol), Z-N-Me-Val-OH (1.23 g, 4.63 mmol) and CMPI (1.2 g, 4.69 mmol) in THF (20 ml), TEA (1.8 ml) was added under cooling with ice and stirred at room temperature for 4 hours. The reaction mixture was mixed with water and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over 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=2:1), giving Z-N-Me-Val-Tyr(3-tBu)-NH2 (1.7 g, 83%).

Workup

  1. temperatureunder cooling with ice
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customto remove the solvent under reduced pressure

Sources & evidence

ORD record
ord-5e3ad171d0eb4b27ac1d36923846a90b
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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