1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → (+)-(2S)-2-(Methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

HRID 1024487

Reaction equation

HRID 1024487 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.[C:19]([NH:26][C@H:27]([C:29]([OH:31])=O)[CH3:28])([O:21][C:22]([CH3:25])([CH3:24])C)=[O:20].[CH3:32]CN=C=NCCCN(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:32][CH2:25][CH:22]([O:21][C:19]([NH:26][C@@H:27]([CH3:28])[C:29]([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:31])=[O:20])[CH3:24]

Participants

6

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 85082Tert-butoxycarbonylalanineHCID 43087680N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine

Product 1

HCID 66726185(+)-(2S)-2-(Methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-2-methylpropan-1-amine (100 mg), Boc-L-alanine (70 mg), EDAC (100 mg), and DMAP (60 mg) in DCM (8 ml) was stirred overnight. The reaction mixture was partitioned between EtOAc and water (8 ml each×3). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purificatied by flash chromatography on silica (33% EtOAc in hexane), which yielded (+)-(2S)-2-(Methylpropan-2-yl)oxycarbonylamino-N-(9-chloro-3,4-dihydro-2H-1,5-benzodioxepin-7-ylmethyl)-N-isobutylpropanamide as a resin: MS (m+1)=441.1. The chiral integrity of this compound was not examined.

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water (8 ml each×3)
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a332bb122c554e289273781fe42a9d10
Source dataset
uspto-grants-2014_05
Patent number
US08722896B2

Linked notes

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