Acetic Acid → (+/-)-2-Methyl-3-((2-nitro)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

HRID 1024491Notes

Reaction equation

HRID 1024491 reaction equation
[CH3:1][CH:2]([CH2:23][NH2:24])[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].[N+:25]([C:28]1[CH:29]=[C:30]([CH:33]=[CH:34][CH:35]=1)C=O)([O-:27])=[O:26].[C:36](O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCl>[CH3:1][CH:2]([CH2:23][NH:24][CH2:36][C:29]1[CH:30]=[CH:33][CH:34]=[CH:35][C:28]=1[N+:25]([O-:27])=[O:26])[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 74493-NitrobenzaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 58080637(+/-)-2-Methyl-3-amino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

Product 1

HCID 58080648(+/-)-2-Methyl-3-((2-nitro)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of (±)-2-Methyl-3-amino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide (94 mg), 3-nitrobenzaldehyde (40 mg), glacial acetic acid (90 μl), and sodium triacetoxyborohydride (78 mg) in dichloromethane (5 ml) was stirred overnight. The reaction mixture was partitioned between aq. K2CO3 (1N, 10 mL) and ethyl acetate (5 ml). The aqueous was washed with EtOAc (5 mL×2). Organic layers were combined, washed with brine, dried with anhydrous sodium sulfate, and concentrated. The residue was purified by flash chromatography on silica (20-50% ethyl acetate in hexane) and yielded (±)-2-Methyl-3-((2-nitro)benzylamino)-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide as a resin: MS (m+1)=490.3.

Workup

  1. customThe reaction mixture was partitioned between aq. K2CO3 (1N, 10 mL) and ethyl acetate (5 ml)
  2. washThe aqueous was washed with EtOAc (5 mL×2)
  3. washwashed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography on silica (20-50% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2b387c4cb8094359aae9b7de74cbea7f
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Reaction notes

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