1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → (+/-)-2-Methyl-3-(methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

HRID 1024488Notes

Reaction equation

HRID 1024488 reaction equation
[Cl:1][C:2]1[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=[C:4]([CH2:13][NH:14][CH2:15][CH:16]([CH3:18])[CH3:17])[CH:3]=1.[CH3:19][CH:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])C)=[O:27])[C:21]([OH:23])=O.Cl.[CH2:34](N=C=NCCCN(C)C)C.CC1C=CN=C(N)C=1C>C(Cl)Cl>[CH3:19][CH:20]([CH2:24][NH:25][C:26]([O:28][CH:29]([CH3:31])[CH2:32][CH3:34])=[O:27])[C:21]([N:14]([CH2:13][C:4]1[CH:3]=[C:2]([Cl:1])[C:7]2[O:8][CH2:9][CH2:10][CH2:11][O:12][C:6]=2[CH:5]=1)[CH2:15][CH:16]([CH3:18])[CH3:17])=[O:23]

Participants

6

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41926403-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acidHCID 110078842-Amino-3,4-dimethylpyridineHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

Product 1

HCID 66726391(+/-)-2-Methyl-3-(methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (600 mg), (±)-2-Methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (200 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (475 mg) and of dimethyl aminopyridine (284 mg) in DCM (30 ml) was stirred overnight. The reaction mixture was partitioned between ethyl acetate and water (30 mL each). The aqueous layer was extracted with EtOAc (30 mL×2). The combined organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by flash chromatography on silica (33% ethyl acetate in hexane) to give (±)-2-Methyl-3-(methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide as a resin: MS (m+1)=455.5.

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water (30 mL each)
  2. extractionThe aqueous layer was extracted with EtOAc (30 mL×2)
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica (33% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2dec416a0723464784cfdb694c18d998
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Reaction notes

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