Acetic Acid → HCID 19094442, compound

HRID 2248289Notes

Reaction equation

HRID 2248289 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[O:10][CH2:9][CH2:8][C:7]([CH2:15][CH2:16][NH:17][O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)([C:11](OC)=[O:12])[C:6]=2[CH:26]=1.C([N-]C(C)C)(C)C.[Li+].C(O)(=O)C>O1CCCC1>[CH2:19]([O:18][N:17]1[CH2:16][CH2:15][C:7]2([C:6]3[CH:26]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=3[O:10][CH2:9][CH2:8]2)[C:11]1=[O:12])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724682Lithium diisopropylamideHCID 19094462HCID 19094462, compound

Product 1

HCID 19094442HCID 19094442, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of methyl 2,3-dihydro-6-fluoro-4-(2-(benzyloxyamino)ethyl)-4H-1-benzopyran-4-carboxylate (3.1 g) in anhydrous tetrahydrofuran at -78° C. was added a solution of 1-M lithium diisopropylamide (9.0 mL) in tetrahydrofuran. After 1 hour acetic acid (1 mL) was added, and the solution concentrated in vacuo. The residue was partitioned between ethyl acetate and 1N HCl, and organic layers washed with 1N HCl, saturated aqueous sodium bicarbonate, brine, dried over sodium sulfate, filtered and evaporated to afford the title compound as an oil, 2.9 g. (1H NMR (CDCl3, 60 MHz): 1.9-2.5 (m, 4H), 3.2-4.6 (m, 4H), 5.0 (s, 2H), 6.3-6.8 (m, 3H), 7.3-7.5 (m, 5H).

Workup

  1. concentrationthe solution concentrated in vacuo
  2. customThe residue was partitioned between ethyl acetate and 1N HCl, and organic layers
  3. washwashed with 1N HCl, saturated aqueous sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-ccb040d2d0bc4a4581ee3dd5926d5832
Source dataset
uspto-grants-1991_08
Patent number
US05039672

Reaction notes

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