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

HRID 1444155ノート

反応式

HRID 1444155 の反応式
[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

参加物

8

反応物 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 14306235Boc-Ile-Pro-OBzl

生成物 1

HCID 131727885Boc-D-Tyr(Me)-L-Ile-L-Pro-OBzl

実験手順

While cooling on ice, TFA (4 mL) was added to Boc-L-Ile-L-Pro-OBzl (1.00 g, 2.6 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 (6 mL), and Boc-D-Tyr(Me)-OH (770 mg, 2.6 mmol) was added. Then while cooling on ice, HOBt.H2O (597 mg, 3.9 mmol), HBTU (1.50 g, 3.9 mmol), and Et3N (0.88 ml, 6.3 mmol) were added, and the mixture was stirred for 16 hours. The reaction solution was concentrated, and extacted with ethyl acetate. The extract was washed 3 times each with 10% aqueous citric acid solution, 4% aqueous sodium bicarbonate solution, and saturated brine, 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, 0.45 (CHCl3/MeOH, 19/1). Yield: 1.17 g (2.06 mmol, 79%).

後処理

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

出典と根拠

ORDレコード
ord-095b40fcad9f4228be433fd905616502
出典データセット
uspto-grants-2010_02
特許番号
US07662778B2

反応ノート

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