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

HRID 1383744Notes

Reaction equation

HRID 1383744 reaction equation
[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:42])[CH3:41])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26].O.C(OCC)(=O)C>C1COCC1.ClC(OCC(C)C)=O.CN1CCOCC1>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([N:23]([CH3:48])[C@H:24]([C:28]([N:30]([CH3:47])[C@H:31]([C:44]([NH2:46])=[O:45])[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[C:35]([C:40]([CH3:43])([CH3:41])[CH3:42])[CH:34]=1)=[O:29])[CH:25]([CH3:27])[CH3:26])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

8

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70878Benzyloxycarbonyl-L-phenylalanineHCID 131722752N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Product 1

HCID 131722753Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2

Reagents, catalysts & solvents 3

HCID 79724-MethylmorpholineSolventHCID 8028TetrahydrofuranSolvent2×HCID 62365Isobutyl chloroformateSolvent

Procedure

To a solution of Z-Phe-OH (742 mg) in THF (3 ml), isobutyl chloroformate (0.32 ml) and NMM (0.27 ml) were added under cooling with ice and the mixture was stirred for 15 minutes. Subsequently, a solution of N-Me-Val-N-Me-Tyr(3-tBu)-NH2 (600 mg) in THF (3 ml) was added and the mixture was stirred at room temperature for 10 hours. Water was added to the reaction mixture and extraction was effected with ethyl acetate. The extract was washed with saturated brine, dried with sodium sulfate, and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2) to give Z-Phe-N-Me-Val-N-Me-Tyr(3-tBu)-NH2 in the amount of 611 mg (58%).

Workup

  1. temperatureunder cooling with ice
  2. stirringthe mixture was stirred at room temperature for 10 hours
  3. washThe extract was washed with saturated brine
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washThe resulting residue was subjected to silica gel column chromatography (eluting solvent; n-hexane:acetone=3:2)

Sources & evidence

ORD record
ord-e8669919cca647fb9505c605464bfc23
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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