Diethyl Ether → HCID 70361669, compound

HRID 1194964Notes

Reaction equation

HRID 1194964 reaction equation
C([O:5][C:6](=[O:43])[C@@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=[O:42])[C@H:13]([CH3:41])[NH:14][CH:15](C(OCC)=O)[CH2:16][CH2:17][CH2:18][CH2:19][CH:20]1[CH2:25][CH2:24][N:23]([C:26]([O:28][CH2:29][C:30]2C=CC=CC=2)=[O:27])[CH2:22][CH2:21]1)(C)(C)C.[BrH:44].C(O)(=O)C.C(OCC)C>C(O)(=O)C>[BrH:44].[BrH:44].[CH2:29]([O:28][C:26]([N:23]1[CH2:24][CH2:25][CH:20]([CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:14][C@H:13]([C:12]([N:8]2[CH2:9][CH2:10][CH2:11][C@H:7]2[C:6]([OH:43])=[O:5])=[O:42])[CH3:41])[CH2:21][CH2:22]1)=[O:27])[CH3:30]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 54290134HCID 54290134, compound

Product 1

HCID 70361669HCID 70361669, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 1.5 ml of acetic acid is dissolved 0.66 g of N-[N-[5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]-L-alanyl]-L-proline tert-butyl ester, and 2 ml of 30% hydrogen bromide-acetic acid solution is added to the solution, followed by standing at room temperature for 1 hour. 50 ml of ethyl ether is added to the reaction solution, followed by shaking, and the precipitate is rinsed twice with 50 ml of ethyl ether. The resulting yellow, viscous material is dissolved in 5 ml of water, and the solution is extracted with 10 ml of ethyl acetate. The aqueous layer is lyophilized to give 0.4 g of N-[N-1-ethoxycarbonyl-5-(4-piperidyl)pentyl]-L-alanyl-L-proline.dihydrobromide.

Workup

  1. additionis added to the solution
  2. washthe precipitate is rinsed twice with 50 ml of ethyl ether
  3. dissolutionThe resulting yellow, viscous material is dissolved in 5 ml of water
  4. extractionthe solution is extracted with 10 ml of ethyl acetate

Sources & evidence

ORD record
ord-5142b50d901a4623a9b0df4550753a50
Source dataset
uspto-grants-1989_03
Patent number
US04816466

Reaction notes

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