Diisopropylethylamine → 4-Amino-3-methyl-5-nitro-phenyl tetrahydro-furan-2-carboxylate

HRID 1846478ノート

反応式

HRID 1846478 の反応式
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([OH:11])=[CH:4][C:3]=1[CH3:12].[O:13]1[CH2:17][CH2:16][CH2:15][C@@H:14]1[C:18](O)=[O:19].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[O:13]1[CH2:17][CH2:16][CH2:15][CH:14]1[C:18]([O:11][C:5]1[CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]([NH2:1])=[C:3]([CH3:12])[CH:4]=1)=[O:19]

参加物

6

反応物 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 2734707Tetrahydro-2-furoic acid, (+)-HCID 669782964-Amino-3-methyl-5-nitrophenol

生成物 1

HCID 669780304-Amino-3-methyl-5-nitro-phenyl tetrahydro-furan-2-carboxylate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

0.84 g (5.00 mmol) 4-amino-3-methyl-5-nitro-phenol, 0.58 g (5.00 mmol) (R)-tetrahydro-furan-2-carboxylic acid, 1.77 g (5.50 mmol) TBTU and 1.92 mL (11.00 mmol) DIPEA in 10.0 mL DMF were stirred overnight at RT. The reaction mixture was poured onto ice water and extracted with ethyl acetate. The organic phase was separated off, dried and evaporated down i.vac. The residue was purified by preparative HPLC-MS. The fractions containing product were partially evaporated down i.vac. and neutralised with an aqueous 1M sodium hydroxide solution. The precipitate formed was suction filtered, washed and dried.

後処理

  1. additionThe reaction mixture was poured onto ice water
  2. extractionextracted with ethyl acetate
  3. customThe organic phase was separated off
  4. customdried
  5. customevaporated down i.vac
  6. customThe residue was purified by preparative HPLC-MS
  7. additionThe fractions containing product
  8. customwere partially evaporated down i.vac
  9. customThe precipitate formed
  10. filtrationfiltered
  11. washwashed
  12. customdried

出典と根拠

ORDレコード
ord-cdd7e279d2364932a105c25296c673b3
出典データセット
uspto-grants-2015_02
特許番号
US08952014B2

反応ノート

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