Dicyclohexylcarbodiimide → HCID 86716157、化合物

HRID 1774448ノート

反応式

HRID 1774448 の反応式
[OH:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2.C1CCC(N=C=NC2CCCCC2)CC1.C1C2C(COC([NH:62][C@H:63]([C:67](O)=[O:68])[CH:64]([CH3:66])[CH3:65])=O)C3C(=CC=CC=3)C=2C=CC=1>CN(C1C=CN=CC=1)C.C(OCC)(=O)C>[NH2:62][C@H:63]([C:67]([O:1][C@H:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C@:3]1([CH2:20][C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[C:11]1[CH2:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:68])[CH:64]([CH3:66])[CH3:65]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 688217FMOC-L-valineHCID 60155116HCID 60155116、化合物

生成物 1

HCID 86716157HCID 86716157、化合物収率 36.3%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 4-(((1R,2R)-1-hydroxy-2,3-dihydro-1H,1′H-[2,2′-biinden]-2-yl)methyl)benzoic acid (230 mg, 0.60 mmol), DCC (148 mg, 0.72 mmol) and DMAP (7 mg, 0.059 mmol) in ethyl acetate (12 mL), was added N-[(9H-fluoren-9-ylmethoxy)carbonyl]-L-valine (193 mg, 0.60 mmol) and then stirred at room temperature for 12 h. The solids were filtered, washed with ethyl acetate (25 ml) and the combined filtrate was washed with 1.5 N HCl (25 mL), water (25 mL), brine (10 mL), dried over anhydrous Na2SO4. The organic layer was evaporated under reduced pressure and the residue 1 (250 mg) was dissolved in dry THF (7 mL) and cooled to 0° C. Dimethylamine (7 mL, 20% in THF) was added drop wise at N2 atmosphere and the reaction mixture was slowly allowed to stir at room temperature for 1 h. The reaction mixture was evaporated under reduced pressure and the residue was purified by CombiFlash using 10% methanol in chloroform as an eluent to yield 105 mg (36%) of the title compound as an off white solid.

後処理

  1. filtrationThe solids were filtered
  2. washwashed with ethyl acetate (25 ml)
  3. washthe combined filtrate was washed with 1.5 N HCl (25 mL), water (25 mL), brine (10 mL)
  4. dry with materialdried over anhydrous Na2SO4
  5. customThe organic layer was evaporated under reduced pressure
  6. dissolutionthe residue 1 (250 mg) was dissolved in dry THF (7 mL)
  7. temperaturecooled to 0° C
  8. additionDimethylamine (7 mL, 20% in THF) was added drop wise at N2 atmosphere
  9. stirringto stir at room temperature for 1 h
  10. customThe reaction mixture was evaporated under reduced pressure
  11. customthe residue was purified by CombiFlash

出典と根拠

ORDレコード
ord-a01b579e74754f92bad981334a618633
出典データセット
uspto-grants-2016_02
特許番号
US09260376B2

反応ノート

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