Tetrahydrofuran → HCID 89802875、化合物

HRID 449819

反応式

HRID 449819 の反応式
[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH:20]1[CH:25]=[C:24]2N=NN(O)[C:23]2=[CH:22][CH:21]=1.[OH2:30].CC[N:33]([CH:37]([CH3:39])[CH3:38])C(C)C.CCN=C=N[CH2:45][CH2:46][CH2:47]N(C)C.C1[CH2:55][O:54]CC1>>[NH:1]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:2]([C:10]([NH:33][C@@H:37]([C:38]([O:54][CH2:55][C:24]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:25]=1)=[O:30])[CH2:39][CH:46]([CH3:47])[CH3:45])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

参加物

6

反応物 5

HCID 8028TetrahydrofuranHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 637610Boc-D-phenylalanineHCID 27960291-Hydroxybenzotriazole hydrate

生成物 1

HCID 89802875HCID 89802875、化合物

実験手順

The synthesis was carried out according to the scheme shown in FIG. 4 (R═CH2Ph). To a suspension of Boc-D-Phe-OH intermediate I-1 (7.96 g, 30.0 mmol), D-Leu-OBn p-TsOH intermediate I-2 (11.80 g, 30.0 mmol), HOBt monohydrate (4.46 g, 33.0 mmol) and DIEA (8.53 g, 66.0 mmol) in anhydrous THF (250 mL) cooled in an ice-water bath was added EDCI (6.33 g, 33.0 mmol) in four portions over 20 minutes with 5 minutes between each addition. The suspension was stirred overnight from a starting temperature of 0° C. to room temperature. After evaporation of THF, the residue was dissolved in ethyl acetate and washed sequentially with 10% citric acid, saturated NaHCO3 and water. The organic phase was dried over sodium sulfate and evaporated under reduced pressure. The residue was dissolved in DCM, passed through a silica gel plug and eluted with 20% ethyl acetate in hexanes. The eluant was evaporated to give the pure product, Boc-D-Phe-D-Leu-OBn, intermediate I-3 (12.40 g, 88%) as a clear oil. LC-MS: m/z=469 (MH).

後処理

  1. temperaturecooled in an ice-water bath
  2. additionbetween each addition
  3. customAfter evaporation of THF
  4. dissolutionthe residue was dissolved in ethyl acetate
  5. washwashed sequentially with 10% citric acid, saturated NaHCO3 and water
  6. dry with materialThe organic phase was dried over sodium sulfate
  7. customevaporated under reduced pressure
  8. dissolutionThe residue was dissolved in DCM
  9. washeluted with 20% ethyl acetate in hexanes
  10. customThe eluant was evaporated

出典と根拠

ORDレコード
ord-8fcf6d81fac4410ea809a8f80d9a32c7
出典データセット
uspto-grants-2013_07
特許番号
US08486894B2

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