HCID 131722733, compound → HCID 44583346, compound

HRID 1383718Notes

Reaction equation

HRID 1383718 reaction equation
[NH:1](C(OC(C)(C)C)=O)[C@H:2]([C:10]([N:12]([CH3:36])[C@H:13]([C:17]([NH:19][C@H:20]([C:33]([NH2:35])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:32])([CH3:31])[CH3:30])[CH:23]=1)=[O:18])[CH:14]([CH3:16])[CH3:15])=[O:11])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)(C(F)(F)F)=O>[NH2:1][C@H:2]([C:10]([N:12]([CH3:36])[C@H:13]([C:17]([NH:19][C@H:20]([C:33]([NH2:35])=[O:34])[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[C:24]([C:29]([CH3:30])([CH3:31])[CH3:32])[CH:23]=1)=[O:18])[CH:14]([CH3:15])[CH3:16])=[O:11])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 1

HCID 131722733HCID 131722733, compound

Product 1

HCID 44583346HCID 44583346, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 380 mg (0.638 mmol) of Boc-Phe-N-Me-Val-Tyr(3-tBu)-NH2 in 15 ml of TFA was stirred at room temperature for one hour and a half. The reaction solution was concentrated under reduced pressure and the resulting residue was diluted with ethyl acetate and washed first with saturated aqueous NaHCO3, then with saturated brine. The organic layer was dried with anhydrous sodium sulfate and concentrated under reduced pressure; thereafter, the resulting residue was subjected to silica gel column chromatography (eluting solvent consisting of methylene chloride, methanol and aqueous ammonia at a ratio of 100:10:1) to give Phe-N-Me-Val-Tyr(3-tBu)-NH2 in the amount of 240 mg (76%) FAB-MS: 497 (M+H+); NMR(method g,CDCl3): δ 0.74(2H,d,J=6.6 Hz), 0.79(1H,d,J=6.6 Hz), 0.89(1H,d,J=6.6 Hz), 0.92(2H,d,J=6.6 Hz), 1.36(3H,s), 1.38(6H,s), 2.27-2.35(1H,m), 2.71(2H,s), 2.81(1H,s), 2.77-3.19(4H,m), 3.56-3.61(2/3H,m), 3.80-3.90(1/3H,m), 3.95(2/3H,d,J=10.9 Hz), 4.46(1/3H,d,J=11.2 Hz), 4.55-4.65(1/3H,m), 4.70-4.85(2/3H,m), 6.60-7.40(8H,m)

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionthe resulting residue was diluted with ethyl acetate
  3. washwashed first with saturated aqueous NaHCO3
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. washeluting solvent

Sources & evidence

ORD record
ord-d11119779273405596cfdc4b999809db
Source dataset
uspto-grants-2001_07
Patent number
US06255285B1

Reaction notes

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