Butyl nitrite → 3-(Dipropylcarbamoyl)benzoic acid

HRID 1014866

反応式

HRID 1014866 の反応式
C(O[C@H:5]1[CH2:9][N:8](C(OC(C)(C)C)=O)[C@@H:7]([C:17](O)=O)[CH2:6]1)C=C.Br[C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:30]([O:32]C)=O)[CH:29]=1)[C:24]([OH:26])=[O:25].N(O[CH2:37]CCC)=O.C(OC(N1C[C@H](O)C[C@@H]1C(O)=O)=O)(C)(C)C>[Cu](Br)Br.O.C(#N)C>[CH2:7]([N:8]([CH2:9][CH2:5][CH3:6])[C:30]([C:28]1[CH:27]=[C:23]([CH:22]=[CH:21][CH:29]=1)[C:24]([OH:26])=[O:25])=[O:32])[CH2:17][CH3:37]

参加物

8

反応物 4

HCID 10996Butyl nitriteHCID 688616N-Boc-cis-4-hydroxy-D-prolineHCID 225936413-Bromo-5-(methoxycarbonyl)benzoic acidHCID 67315699(4R)-1-Boc-4-(2-propen-1-yloxy)-D-proline

生成物 1

HCID 1827693-(Dipropylcarbamoyl)benzoic acid収率 97%

試薬・触媒・溶媒 3

HCID 24611Copper bromide (CuBr2)触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒

実験手順

Step G (2): 3-bromo-5-(methoxycarbonyl)benzoic acid. To a mixture of copper (II) bromide (5.5 g, 24.6 mmol), n-butyl nitrite (3.17 g, 30.75 mmol) and acetonitrile (300 mL) was added 3-amino-5-(methoxycarbonyl)benzoic acid (Step G (1), 4.0 g, 20.5 mmol) in aceonitrile (300 mL) over 30 min at 0° C. and the mixture was warmed up and stirred at rt for 3 h. H2O was added and acetonitrile was removed. Ethyl acetate (600 mL) was added and the mixture was washed with 3N HCl, H2O, dried over Na2SO4, and concentrated in vacuo to give the title compound (97% yield): 1H NMR (CDCl3, 500 MHz) δ ppm 3.96 (3H, s), 8.41 (1H, s), 8.41 (1H, s), 8.67 (1H, m). MS (ESI) (M−H)− 259.02.

後処理

  1. temperaturethe mixture was warmed up
  2. customacetonitrile was removed
  3. additionEthyl acetate (600 mL) was added
  4. washthe mixture was washed with 3N HCl, H2O
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-7e4cf51a9ccc4cd58d94b5cebc37a06a
出典データセット
uspto-grants-2011_07
特許番号
US07981913B2

関連ノート

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