Water → Boc-D-Tyr(Me)-L-Ile-D-Pro-OBzl

HRID 1444157Notes

Reaction equation

HRID 1444157 reaction equation
[C:1]([OH:7])([C:3](F)(F)F)=[O:2].[NH:8](C(OC(C)(C)C)=O)[C@H:9]([C:14]([N:16]1C[CH2:29][CH2:28][C@@H:17]1C(OCC1C=CC=CC=1)=O)=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11].[NH:38]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C@@H:39]([C:49]([OH:51])=O)[CH2:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][CH3:48])=[CH:43][CH:42]=1.[CH:59]1[CH:60]=[CH:61][C:62]2N(O)N=N[C:63]=2[CH:64]=1.O.[CH3:70]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(CC)CC>>[NH:38]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[C@@H:39]([C:49]([NH:8][C@H:9]([C:14]([N:16]1[CH2:17][CH2:28][CH2:29][C@@H:3]1[C:1]([O:7][CH2:70][C:63]1[CH:62]=[CH:61][CH:60]=[CH:59][CH:64]=1)=[O:2])=[O:15])[C@H:10]([CH2:12][CH3:13])[CH3:11])=[O:51])[CH2:40][C:41]1[CH:42]=[CH:43][C:44]([O:47][CH3:48])=[CH:45][CH:46]=1

Participants

8

Reactant 7

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 7017908Boc-O-methyl-D-tyrosineHCID 58726192HCID 58726192, compound

Product 1

HCID 58726683Boc-D-Tyr(Me)-L-Ile-D-Pro-OBzl

Procedure

While cooling on ice, TFA (5 mL) was added to Boc-L-Ile-D-Pro-OBzl (1.63 g, 3.38 mmol), and this was left to stand for 30 minutes. TFA was removed by evaporation, and the residue was dried under reduced pressure. This was dissolved in DMF (8 mL), Boc-D-Tyr(Me)-OH (1.50 g, 5.07 mmol) was added, and while cooling on ice, HOBt.H2O (518 mg, 3.38 mmol), HBTU (1.92 g, 5.07 mmol), and Et3N (2.37 ml, 16.9 mmol) were added, and this mixture was stirred for 3 hours. The reaction solution was concentrated, extracted with ethyl acetate, the extract was washed 3 times each with 10% aqueous citric acid solution, 4% aqueous sodium bicarbonate solution, and saturated bee, and dried over magnesium sulfate, and then ethyl acetate was removed by evaporation. Purification by silica gel chromatography yielded the desired product as a foam (column: Merck Kieselgel 60 Φ 3.4×30 cm, eluent: CHCl3/MeOH, 99/1). TLC: Rf, 0.89 (CHCl3/MeOH, 9/1). Yield: 1.44 g (2.42 mmol, 72%).

Workup

  1. waitthis was left
  2. customTFA was removed by evaporation
  3. customthe residue was dried under reduced pressure
  4. dissolutionThis was dissolved in DMF (8 mL)
  5. concentrationThe reaction solution was concentrated
  6. extractionextracted with ethyl acetate
  7. washthe extract was washed 3 times each with 10% aqueous citric acid solution, 4% aqueous sodium bicarbonate solution, and saturated bee
  8. dry with materialdried over magnesium sulfate
  9. customethyl acetate was removed by evaporation
  10. customPurification by silica gel chromatography

Sources & evidence

ORD record
ord-80c4e58623cb41e9809103b5ba8815df
Source dataset
uspto-grants-2010_02
Patent number
US07662778B2

Reaction notes

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