Water → HCID 66726093, compound

HRID 1024495Notes

Reaction equation

HRID 1024495 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][C:10]([CH2:12][CH2:13][CH:14]([NH2:18])[CH:15]([CH3:17])[CH3:16])=[CH:11][C:6]=2[O:5][CH2:4][CH2:3][CH2:2]1.[CH3:19][CH:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[C:21](O)=[O:22].Cl.C(N=C=NCCCN(C)C)C.O>CN(C1C=CN=CC=1)C.ClCCl>[CH3:19][CH:20]([CH2:24][NH:25][C:26]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:27])[C:21]([NH:18][CH:14]([CH:15]([CH3:16])[CH3:17])[CH2:13][CH2:12][C:10]1[CH:9]=[CH:8][C:7]2[O:1][CH2:2][CH2:3][CH2:4][O:5][C:6]=2[CH:11]=1)=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41926403-((tert-Butoxycarbonyl)amino)-2-methylpropanoic acidHCID 64503459HCID 64503459, compound

Product 1

HCID 66726093HCID 66726093, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

50 mg of (±)-1-(3,4-dihydro-2H-1,5-benzodioxepine-7-yl)-4-methylpentan-3-ylamine was mixed with of (±)-2-Methyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid (25 mg), 1-ethyl-3-(3-dimethylaminopropyl)-carbodiimide hydrochloride (53 mg), and DMAP (33 mg) in dichloromethane (5 ml) and stirred overnight. Water (5 ml) was added, and the reaction mixture was extracted with ethyl acetate (5 ml three times). The organic layer was washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography on silica (20% ethyl acetate in hexane) yielded a resin: MS (m+1)=435.6.

Workup

  1. extractionthe reaction mixture was extracted with ethyl acetate (5 ml three times)
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification by flash chromatography on silica (20% ethyl acetate in hexane)
  6. customyielded a resin

Sources & evidence

ORD record
ord-0e2f1b1c71d04acfa91ac8070a747b4b
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Reaction notes

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