1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 53764670, compound

HRID 849875Notes

Reaction equation

HRID 849875 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([OH:16])=O)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[NH2:38][C@H:39]([CH2:68][C:69]1[CH:78]=[CH:77][C:76]2[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=2)[CH:70]=1)[C:40]([NH:42][C@@H:43]([C:55]1[N:59]([CH2:60][CH2:61][C:62]2[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=2)[N:58]=[N:57][N:56]=1)[CH2:44][C:45]1[CH:54]=[CH:53][C:52]2[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=2)[CH:46]=1)=[O:41]>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14](=[O:16])[NH:38][C@@H:39]([C:40](=[O:41])[NH:42][C@@H:43]([C:55]2[N:59]([CH2:60][CH2:61][C:62]3[CH:63]=[CH:64][CH:65]=[CH:66][CH:67]=3)[N:58]=[N:57][N:56]=2)[CH2:44][C:45]2[CH:54]=[CH:53][C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[CH:46]=2)[CH2:68][C:69]2[CH:78]=[CH:77][C:76]3[C:71](=[CH:72][CH:73]=[CH:74][CH:75]=3)[CH:70]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 3928711-(tert-Butoxycarbonyl)-4-piperidinecarboxylic acidHCID 53918877HCID 53918877, compound

Product 1

HCID 53764670HCID 53764670, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N-tert-butyloxycarbonylpiperidine-4-carboxylic acid (68 mg; 0.296 mmol) was dissolved in methylene chloride (7 ml). HOBT (40 mg; 0.296 mmol) and EDAC (62 mg; 0.326 mmol) were added and the mixture was stirred 15 min at RT. (2R)-2-Amino-3-(2-naphthyl)-N-((1R)-2-(2-naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethyl)propionamide (152 mg; 0.296 mmol) was added and stirring was continued overnight. Methylene chloride (25 ml) was added. The organic phase was washed with aqueous sodium hydrogencarbonate (25 ml), aqueous sodium hydrogensulfate (10%; 25 ml) and water (25 ml). The organic phase was dried (Magnesium sulfate) and the solvent removed in vacuo to afford 170 mg of 4-((1R)-2-(2-Naphthyl)-1-((1R)-2-(2-naphthyl)-1-(1-phenethyl-1H-tetrazol-5-yl)ethylcarbamoyl)ethylcarbamoyl)piperidine-1-carboxylic acid tert-butylester.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. washThe organic phase was washed with aqueous sodium hydrogencarbonate (25 ml), aqueous sodium hydrogensulfate (10%; 25 ml) and water (25 ml)
  4. dry with materialThe organic phase was dried (Magnesium sulfate)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-fb5d8c4885b04a7292a3234a0dc1cded
Source dataset
uspto-grants-2000_01
Patent number
US06013658

Reaction notes

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