1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 178513881, compound

HRID 1351903Notes

Reaction equation

HRID 1351903 reaction equation
C(OC([N:8](C1CC2C=C(OCC(O)=O)C=CC=2CCC1)[CH2:9][C@H:10](O)[CH2:11][O:12]C1C=CC=CC=1)=O)(C)(C)C.CN(C)CCCN=C=NCC.O[N:48]1C2C=CC=CC=2[N:50]=[N:49]1.O.[NH2:58]C1NN=NN=1>ClCCl>[NH:48]1[C:9]([CH2:10][C:11]([NH2:58])=[O:12])=[N:8][N:50]=[N:49]1

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 57108693HCID 57108693, compoundHCID 178509300HCID 178509300, compound

Product 1

HCID 178513881HCID 178513881, compoundYield 210.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-[8-[N-tert-butoxycarbonyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]acetic acid (100 mg), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (61 mg) and 1-hydroxybenzotriazole (33 mg) in dichloromethane (10 ml) was added 5-aminotetrazole monohydrate (19.3 mg). The resulting mixture was stirred at room temperature for 18 hours and extracted with ethyl acetate. The extract was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed (hexane-ethyl acetate) over silica gel and treated with 4N hydrogen chloride in ethyl acetate to afford 2-[8-[(2S)-2-hydroxy-3-phenoxypropyl)-amino]-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy]-2-(tetrazol-5-yl)acetamide (50 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was chromatographed (hexane-ethyl acetate) over silica gel
  6. additiontreated with 4N hydrogen chloride in ethyl acetate

Sources & evidence

ORD record
ord-b6ff9f9330ac4d4e9e91e7ea058d2b30
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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