Triacetoxyperiodinane → (3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1158337

反応式

HRID 1158337 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:33])[CH3:32])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH2:34][OH:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.CCOCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([CH2:13][N:14]([CH:31]([CH3:32])[CH3:33])[C:15](=[O:30])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[C:18]([O:24][CH2:25][CH2:26][CH2:27][O:28][CH3:29])[CH:17]=2)[C@H:10]([CH:34]=[O:35])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 159087TriacetoxyperiodinaneHCID 59512299(3S,4R)-3-Hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

生成物 1

HCID 59512275(3S*,4R*)-3-formyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒3 回

実験手順

To a well-stirred mixture of (3S*,4R*)-3-hydroxymethyl-4-({isopropyl-[4-methoxy-3-(3-methoxy-propoxy)-benzoyl]-amino}-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester (600 mg, 1.21 mmol) and Dess-Martin periodinane (272 mg, 1.21 mmol) in CH2Cl2 (10 mL), slowly wet CH2Cl2 (24 μL of water in 2 mL of CH2Cl2) is added. The clear solution becomes cloudy towards the end of wet CH2Cl2 addition. The mixture is diluted with Et2O and concentrated to a few mL of solvent by rotary evaporation. The residue is taken up in Et2O, and washed with a 1:1 10% Na2S2O3/saturated aqueous solution of NaHCO3, followed by H2O and brine. The aqueous washings are back-extracted with Et2O, and this organic layer is washed with H2O and brine. The combined organic layers are dried over Na2SO4, filtered and concentrated under reduced pressure. The crude material is used without further purification in the next step. TLC, Rf (CH2Cl2/MeOH 95:5)=0.3. tR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min): 5.16 min.

後処理

  1. additionis added
  2. concentrationconcentrated to a few mL of solvent by rotary evaporation
  3. washwashed with a 1:1 10% Na2S2O3/saturated aqueous solution of NaHCO3
  4. extractionThe aqueous washings are back-extracted with Et2O
  5. washthis organic layer is washed with H2O and brine
  6. dry with materialThe combined organic layers are dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe crude material is used without further purification in the next step
  10. customtR (HPLC, Nucleosil C18 column, 10-100% CH3CN/H2O/5 min, 100% CH3CN/3 min, CH3CN and H2O containing 0.1% TFA, flow: 1.5 ml/min)
  11. custom5.16 min.

出典と根拠

ORDレコード
ord-2ffd5e2276b146acb956c884f5a8c730
出典データセット
uspto-grants-2010_10
特許番号
US07807709B2

関連ノート

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