Diisopropylethylamine → (9H-fluoren-9-yl)methyl(S)-1-((S)-(1,1-diethoxypropan-2-yl)(benzyl)amino)-1-oxopropan-2-ylcarbamate

HRID 576869

反応式

HRID 576869 の反応式
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@@H:19]([CH3:23])[C:20](O)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.[CH2:48]([NH:55][C@@H:56]([CH3:64])[CH:57]([O:61][CH2:62][CH3:63])[O:58][CH2:59][CH3:60])[C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1.CCN(C(C)C)C(C)C>ClCCl.C(OCC)(=O)C>[CH2:62]([O:61][CH:57]([O:58][CH2:59][CH3:60])[C@@H:56]([N:55]([CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)[C:20](=[O:21])[C@@H:19]([NH:18][C:16](=[O:17])[O:15][CH2:14][CH:12]1[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[C:5]2[C:13]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[CH3:23])[CH3:64])[CH3:63]

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 6364642N-((9H-Fluoren-9-ylmethoxy)carbonyl)-L-alanineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66978105(S)-N-benzyl-1,1-diethoxypropan-2-amine2 回

生成物 1

HCID 86663942(9H-fluoren-9-yl)methyl(S)-1-((S)-(1,1-diethoxypropan-2-yl)(benzyl)amino)-1-oxopropan-2-ylcarbamate収率 45.2%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of (S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)propanoic acid 68 mg (0.22 mmol) and O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate 84 mg (0.22 mmol) in dichloromethane 1 ml, a solution of (S)—N-benzyl-1,1-diethoxypropan-2-amine (Compound IV-15) 47 mg (0.2 mmol) and N,N′-diisopropylethylamine 38 ml (0.22 mmol) in dichloromethane 1 ml was added and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate 50 ml and washed with saturated aqueous sodium bicarbonate 50 ml, water 50 ml and brine 50 ml. The organic phase was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo and the residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=9:1 to 7:3) to obtain the title compound 48 mg (45%).

後処理

  1. washwashed with saturated aqueous sodium bicarbonate 50 ml, water 50 ml and brine 50 ml
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified on silica gel column chromatography (n-hexane:ethyl acetate=9:1 to 7:3)

出典と根拠

ORDレコード
ord-7da1a46a181d46ccbd34358cbf58d52e
出典データセット
uspto-grants-2015_05
特許番号
US09040531B2

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