Diisopropylcarbodiimide → Boc-Val-N-Me-Tyr(3-tBu)-NH2

HRID 1383721Notes

Reaction equation

HRID 1383721 reaction equation
[NH:1]([CH3:18])[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.[NH:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:20]([C:24]([OH:26])=O)[CH:21]([CH3:23])[CH3:22].C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CN(C=O)C.C(OCC)(=O)C>[NH:19]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C@H:20]([C:24]([N:1]([CH3:18])[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]([CH3:12])([CH3:13])[CH3:14])[CH:5]=1)=[O:26])[CH:21]([CH3:22])[CH3:23]

Participants

7

Reactant 4

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 83693Boc-L-ValineHCID 131722738N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 131722737Boc-Val-N-Me-Tyr(3-tBu)-NH2

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 120 mg (0.480 mmol) of N-Me-Tyr(3-tBu)-NH2,156 mg (0.718 mmol) of Boc-Val-OH and 110 mg (0.718 mmol) of HOBT in 2 ml of DMF, 0.111 ml (0.718 mmol) of DIC was added under cooling with ice and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed first with saturated aqueous NaHCO3, then with water, and finally with saturated brine. The organic layer was dried with anhydrous magnesium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=2:1) to give Boc-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 147 mg (68%).

Workup

  1. temperatureunder cooling with ice
  2. washwashed first with saturated aqueous NaHCO3
  3. dry with materialThe organic layer was dried with anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washthe resulting residue was subjected to silica gel column chromatography (eluting solvent; ethyl acetate:n-hexane=2:1)

Sources & evidence

ORD record
ord-0d204a0797534ef3ab91a35c03961ccc
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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