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

HRID 1846478Notes

Reaction equation

HRID 1846478 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-cdd7e279d2364932a105c25296c673b3
Source dataset
uspto-grants-2015_02
Patent number
US08952014B2

Reaction notes

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