Diisopropylcarbodiimide → Boc-Phe-N-Me-Val-Tyr(3-tBu) NH3

HRID 1383717Notes

Reaction equation

HRID 1383717 reaction equation
C([N:11]([CH3:35])[C@H:12]([C:16]([NH:18][C@H:19]([C:32](N)=[O:33])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=1)=[O:17])[CH:13]([CH3:15])[CH3:14])(OCC1C=CC=CC=1)=O.[NH:36](C)[C@H](C(N[C@H](C(N)=O)CC1C=CC(O)=C(C(C)(C)C)C=1)=[O:42])C(C)C.[NH:61]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[C@H:62]([C:70]([OH:72])=O)[CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1.C1C=CC2N(O)N=NC=2C=1.CC(C)N=C=NC(C)C>CO.CN(C=O)C.C(OCC)(=O)C.[C].[Pd]>[NH:61]([C:73]([O:75][C:76]([CH3:79])([CH3:78])[CH3:77])=[O:74])[C@H:62]([C:70]([N:11]([CH3:35])[C@H:12]([C:16]([NH:18][C@H:19]([C:32]([OH:33])=[O:42])[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([C:28]([CH3:29])([CH3:30])[CH3:31])[CH:22]=1)=[O:17])[CH:13]([CH3:14])[CH3:15])=[O:72])[CH2:63][C:64]1[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=1.[NH3:36]

Participants

10

Reactant 5

HCID 12734DiisopropylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 131722729Z-N-Me-Val-Tyr(3-tBu)-NH2HCID 131722732N-Me-Val-Tyr(3-tBu)-NH2

Product 1

HCID 131722730Boc-Phe-N-Me-Val-Tyr(3-tBu) NH3

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 810 mg of Z-N-Me-Val-Tyr(3-tBu)-NH2 and 300 mg of 10% palladium carbon in 50 ml of methanol was stirred under a hydrogen stream for 13 hours and a half. The reaction mixture was filtered and the filtrate was distilled off under reduced pressure. To a solution in DMF (12 ml) of 470 mg (1.35 mmol) of the resulting N-Me-Val-Tyr(3-tBu)-NH2, 390 mg (1.48 mmol) of Boc-Phe-OH and 230 mg (1.48 mmol) of HOBT, 0.23 ml (1.48 mmol) of DIC was added dropwise under cooling with ice and the mixture was stirred at room temperature for 13 hours and a half. The reaction mixture was diluted with ethyl acetate and washed with saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure; the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of methylene chloride, methanol and aqueous ammonia at a ratio of 100:3:1) to give Boc-Phe-N-Me-Val-Tyr(3-tBu)-NH3 in the amount of 380 mg (47%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. distillationthe filtrate was distilled off under reduced pressure
  3. temperatureunder cooling with ice
  4. stirringthe mixture was stirred at room temperature for 13 hours
  5. washwashed with saturated brine
  6. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  7. concentrationconcentrated under reduced pressure
  8. washeluting solvent

Sources & evidence

ORD record
ord-54d1d0b0a9bc4b7d91976930bd96b974
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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