1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 59361606, compound

HRID 1893224Notes

Reaction equation

HRID 1893224 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH2:12])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:13][C:14]([F:29])([F:28])[C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[C:18]([NH:20][CH2:21][C:22](O)=[O:23])=[O:19].CCN=C=NCCCN(C)C.C1C=CC2N(O)N=NC=2C=1>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([NH:12][C:22](=[O:23])[CH2:21][NH:20][C:18](=[O:19])[C:17]2[CH:25]=[CH:26][CH:27]=[C:15]([C:14]([F:13])([F:29])[F:28])[CH:16]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 1516507Tert-butyl 3-aminoazetidine-1-carboxylateHCID 2777432((3-(Trifluoromethyl)benzoyl)amino)acetic acid

Product 1

HCID 59361606HCID 59361606, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-amino-azetidine-1-carboxylic acid tert-butyl ester (BetaPharma, 1.2 g, 6.97 mmol) and (3-trifluoromethyl-benzoylamino)-acetic acid (Bionet, 1.57 g, 6.36 mmol) in DCM (10 mL) was treated with EDCI (Aldrich, 1.57 g, 6.36 mmol) and HOBT (Aldrich, 1.22 g, 6.36 mmol) at room temperature for 4 hours. The reaction solution was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated to give a yellow oil, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as a white solid.

Workup

  1. customThe reaction solution was partitioned between DCM and water
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a yellow oil, which
  7. customwas then purified by silica gel column on a CombiFlash® system

Sources & evidence

ORD record
ord-d8ea516a503f421aab9e7fa813ccb850
Source dataset
uspto-grants-2013_08
Patent number
US08513229B2

Reaction notes

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