1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 57000309, compound

HRID 1033857Notes

Reaction equation

HRID 1033857 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C@H:7]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[C:8]([OH:10])=O.Br.[CH2:23]([O:30][C:31]([C:33]1[N:34]=[CH:35][O:36][C:37]=1[CH2:38][CH2:39][NH2:40])=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C>C(N(CC)CC)C.CN(C)C=O>[CH2:23]([O:30][C:31]([C:33]1[N:34]=[CH:35][O:36][C:37]=1[CH2:38][CH2:39][NH:40][C:8](=[O:10])[C@@H:7]([NH:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:6][C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:32])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 22403421HCID 22403421, compoundHCID 53725744(2S)-2-Amino-3-(thien-2-yl)propanoic acid, N-CBZ protected

Product 1

HCID 57000309HCID 57000309, compoundYield 89.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8471TriethylamineSolvent

Conditions

Temperature
-20 °C

Procedure

A mixture of 2.56 g of (2S)-3-(2-thienyl)-2-(benzyloxycarbonylamino)propionic acid, 2.39 g of 4-benzyloxycarbonyl-5-(2-aminoethyl)oxazole.hydrobromide, 1.42 g of 1-hydroxybenzotriazole hydrate and 30 ml of dimethylformamide was cooled to -20° C., and 1.77 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide.hydrochloride was added thereto. After 10 minutes, 0.93 g of triethylamine was added to the mixture, and the temperature of the mixture was gradually returned to room temperature and the mixture was stirred overnight. The solvent was removed, and ethyl acetate was added to the residue. The mixture was washed and dried, and then the solvent was removed. The residue was purified by silica gel column chromatography (solvent: chloroform:ethyl acetate=19:1) to obtain 3.5 g of 4-benzyloxycarbonyl-5-{2-[N-((2S)-3-(2-thienyl)-2-(benzyloxycarbonylamino)propionyl)amino]ethyl}oxazole as syrup.

Workup

  1. customwas gradually returned to room temperature
  2. customThe solvent was removed
  3. additionethyl acetate was added to the residue
  4. washThe mixture was washed
  5. customdried
  6. customthe solvent was removed
  7. customThe residue was purified by silica gel column chromatography (solvent: chloroform:ethyl acetate=19:1)

Sources & evidence

ORD record
ord-04e336daf469487181c228619c6cb27d
Source dataset
uspto-grants-1994_05
Patent number
US05312826

Reaction notes

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