Water → Z-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1988230Notes

Reaction equation

HRID 1988230 reaction equation
[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([OH:18])=O)[CH:13]([CH3:15])[CH3:14])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[NH:20]([CH3:37])[C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:33])([CH3:32])[CH3:31])[CH:24]=1.O>C1COCC1>[C:1]([N:11]([CH3:19])[C@H:12]([C:16]([N:20]([CH3:37])[C@H:21]([C:34]([NH2:36])=[O:35])[CH2:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[C:25]([C:30]([CH3:31])([CH3:32])[CH3:33])[CH:24]=1)=[O:18])[CH:13]([CH3:14])[CH3:15])([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7016371N-Methyl-N-[(phenylmethoxy)carbonyl]-L-valineHCID 131722738N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 131722751Z-N-Me-Val-N-Me-Tyr(3-tBu)-NH2Yield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of Z-N-Me-Val-OH (700 mg, 2.64 mmol), N-Me-Tyr(3-tBu)-NH2 (0.55 g, 2.20 mmol) and CMPI (674 mg 2.64 mmol) in THF (22 ml), under cooling with ice, TEA (0.61 ml) was added and stirred at room temperature overnight. 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=3:2) to give Z-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (0.98 g, 90%).

Workup

  1. additionwas added
  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-ed2140e61b4848978f651f337a79c2cc
Source dataset
uspto-grants-2009_06
Patent number
US07553969B1

Reaction notes

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