Aluminum(III) Chloride → HCID 58303977, compound

HRID 1404131Notes

Reaction equation

HRID 1404131 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Al+3].[Cl-].[Cl-].[Cl-].[CH2:11]([NH:18][C:19](=O)[CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:33])[C:28]=2[O:30][CH2:31][CH3:32])[N:23]([CH3:34])[CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>C1COCC1>[CH2:11]([NH:18][CH2:19][CH2:20][C:21]1[C:29]2[C:24](=[CH:25][CH:26]=[C:27]([F:33])[C:28]=2[O:30][CH2:31][CH3:32])[N:23]([CH3:34])[CH:22]=1)[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 21226445Aluminium lithium hydrideHCID 66927211HCID 66927211, compound

Product 1

HCID 58303977HCID 58303977, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LiAlH4 (5 mg, 0.12 mmol) and AlCl3 (16 mg, 0.12 mmol) in THF (5 mL) was added a solution of 30-14 (14 mg, 0.04 mmol) in THF (5 mL) dropwise, the mixture was stirred at room temperature overnight before Na2SO4.10H2O was added. The mixture was filtered and the filtrate was evaporated to give a crude product which was purified by preparative HPLC (acid condition, water/CH3CN, 25-30% CH3CN in 7.5 min, RT=6.5 min) to afford 30-15 (8 mg, 61%) as a yellow solid. 1H-NMR (400 MHz, CDCl3): δ (ppm) 7.30-7.28 (m, 5H), 7.00-6.95 (m, 1H), 6.87-6.84 (m, 2H), 4.24 (q, J=7.2 Hz, 2H), 4.01-3.98 (br.s, 2H), 3.67 (s, 3H), 3.27-3.22 (br.s, 2H), 3.15-3.11 (br.s, 2H), 1.34 (t, J=6.8 Hz, 3H). LRMS: calc 326.2 and found: 327.0 [M+1].

Workup

  1. additionwas added
  2. filtrationThe mixture was filtered
  3. customthe filtrate was evaporated
  4. customto give a crude product which
  5. customwas purified by preparative HPLC (acid condition, water/CH3CN, 25-30% CH3CN in 7.5 min, RT=6.5 min)

Sources & evidence

ORD record
ord-b228600d0ea84593aeaf635a9c3ae596
Source dataset
uspto-grants-2014_12
Patent number
US08912220B2

Reaction notes

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