Benzyl Alcohol → HCID 67491122、化合物

HRID 571953ノート

反応式

HRID 571953 の反応式
C([N:3]([CH2:6][CH3:7])[CH2:4]C)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:15])C=CC=CC=1.[C:25]([O:29][C:30]([NH:32][C@@H:33]1[CH2:38]CC[C@H:35](C(O)=O)[CH2:34]1)=[O:31])([CH3:28])([CH3:27])[CH3:26].[CH2:42]([OH:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1>C1(C)C=CC=CC=1.CCOC(C)=O>[C@H:6]1([NH:3][C:4](=[O:15])[O:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[CH2:7][CH2:35][CH2:34][C@@H:33]([NH:32][C:30](=[O:31])[O:29][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:38]1

参加物

7

反応物 4

HCID 244Benzyl AlcoholHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 2755995rel-(1R,3S)-3-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclohexanecarboxylic acid

生成物 1

HCID 67491122HCID 67491122、化合物

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Triethylamine (1.8 mL, 12.9 mmol) and diphenylphosphoryl azide (2.0 mL, 9.27 mmol) were added to a stirred solution of cis-3-[(tert-butoxycarbonyl)amino]cyclohexanecarboxylic acid (2.0 g, 8.22 mmol) in toluene (50 mL), and the resulting mixture was stirred at rt for 3 h. Benzyl alcohol (1.70 mL, 16.4 mmol) was added, and the mixture was heated to 100° C. After 12 h, the reaction mixture was cooled to rt, diluted with EtOAc, and the resulting mixture was washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 0-30% EtOAc/hexanes as eluent) to afford the title compound i-1a. m/z (ES) 371 (M+Na)+

後処理

  1. temperaturethe mixture was heated to 100° C
  2. waitAfter 12 h
  3. temperaturethe reaction mixture was cooled to rt
  4. washthe resulting mixture was washed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 0-30% EtOAc/hexanes as eluent)

出典と根拠

ORDレコード
ord-52d1315c05e64c4f9329851e4db61ded
出典データセット
uspto-grants-2015_05
特許番号
US09029377B2

反応ノート

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