Acetic Acid → HCID 46831591, compound

HRID 1024490Notes

Reaction equation

HRID 1024490 reaction equation
[CH3:1][CH:2]([CH2:23][NH:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:3]([N:5]([CH2:10][C:11]1[CH:21]=[C:20]([Cl:22])[C:14]2[O:15][CH2:16][CH2:17][CH2:18][O:19][C:13]=2[CH:12]=1)[CH2:6][CH:7]([CH3:9])[CH3:8])=[O:4].C=O.[C:34](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>O1CCCC1>[CH3:1][CH:2]([CH2:23][N:24]([CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)[CH3:34])[C:3]([N:5]([CH2:10][C:11]1[CH:21]=[C:20]([Cl:22])[C:14]2[O:15][CH2:16][CH2:17][CH2:18][O:19][C:13]=2[CH:12]=1)[CH2:6][CH:7]([CH3:8])[CH3:9])=[O:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 46831592HCID 46831592, compound

Product 1

HCID 46831591HCID 46831591, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (±)-2-Methyl-3-(benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide (26 mg), paraformaldehye (16 mg), glacial acetic acid (90 μl) and sodium triacetoxyborohydride (26 mg) was dissolved in tetrahydrofuran (5 ml), and stirred overnight. The mixture was partitioned between aq. potassium carbonate (1N, 10 mL) and ethyl acetate (15 ml). The organic layer was concentrated and the residue was purified by flash chromatography on silica (40% ethyl acetate in hexane) to yield a resin: MS (m+1)=459.2; H NMR (500 MHz, CDCl3) 0.95 (m, 6H), 2.00 (m, 1H), 2.05 (m, 1H), 2.25 (m, 2H), 2.30 (m, 3H), 2.55 (t, 1H), 2.65 (t, 1H), 2.90 (m, 1H), 3.05 (d, 1H), 3.25 (d, 1H), 3.60 (m, 2H), 4.15 (m, 2H), 4.35 (m, 2H), 4.50 (m, 2H), 6.6-7.0 (m, 2H), 7.0-7.5 (m, 5H).

Workup

  1. customThe mixture was partitioned between aq. potassium carbonate (1N, 10 mL) and ethyl acetate (15 ml)
  2. concentrationThe organic layer was concentrated
  3. customthe residue was purified by flash chromatography on silica (40% ethyl acetate in hexane)
  4. customto yield a resin

Sources & evidence

ORD record
ord-664a6c2963b04492994999925fc0ad28
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Reaction notes

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