Dicyclohexylcarbodiimide → HCID 59401250、化合物

HRID 77029

反応式

HRID 77029 の反応式
[C:1]1([CH:7]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1CCC(N=[C:25]=[N:26][CH:27]2[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]2)CC1.C1C=CC2N(O)N=NC=2C=1.CN1CCCC(O)CC1>C1COCC1>[CH3:25][N:26]1[CH2:27][CH2:32][CH2:31][CH:30]([O:9][C:8](=[O:10])[CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:29][CH2:28]1

参加物

6

反応物 4

HCID 10868DicyclohexylcarbodiimideHCID 19375alpha-(Phenylamino)benzeneacetic acidHCID 757711-HydroxybenzotriazoleHCID 109755091-Methylazepan-4-ol

生成物 1

HCID 59401250HCID 59401250、化合物収率 20.3%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 2-phenyl-2-(phenylamino)acetic acid (I1) (175 mg, 0.77 mmol), DCC (192 mg, 0.92 mmol), HOBt (124 mg, 0.92 mmol) and 1-methyl-azepan-4-ol (100 mg, 0.77 mmol) in dry THF (100 mL) is stirred at RT overnight under nitrogen flowstream (UPLC-MS monitoring: complete conversion). The solvent is evaporated and the residue is taken up with aq. HCl and washed with EtOAc. The aqueous phase is basified with NaHCO3 and extracted with DCM (three times). The organic layers are combined, dried over Na2SO4, filtered and evaporated to dryness. The resulting crude is first purified by flash chromatography (DCM to DCM/MeOH=95/5) and then by preparative LC-MS. The purified compound is partitioned between sat. NaHCO3 and DCM, the organic phase is dried over Na2SO4, filtered and evaporated under vacuum to give 53 mg of the title compound as brown oil (20% yield, mixture of diastereoisomers).

後処理

  1. customThe solvent is evaporated
  2. washwashed with EtOAc
  3. extractionextracted with DCM (three times)
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe resulting crude is first purified by flash chromatography (DCM to DCM/MeOH=95/5)
  8. customThe purified compound is partitioned between sat. NaHCO3 and DCM
  9. dry with materialthe organic phase is dried over Na2SO4
  10. filtrationfiltered
  11. customevaporated under vacuum

出典と根拠

ORDレコード
ord-0605cbee109747b89d917af46f3abb88
出典データセット
uspto-grants-2014_09
特許番号
US08835682B2

関連ノート

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