Diethyl Ether → HCID 18631453, compound

HRID 1194960Notes

Reaction equation

HRID 1194960 reaction equation
C([O:5][C:6](=[O:49])[CH2:7][N:8]([C:18](=[O:48])[C@H:19]([CH3:47])[NH:20][C@@H:21]([C:42]([O:44][CH2:45][CH3:46])=[O:43])[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[CH2:31][CH2:30][N:29](C(OCC2C=CC=CC=2)=O)[CH2:28][CH2:27]1)[CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)(C)(C)C.[BrH:50].C(O)(=O)C.C(OCC)C>C(O)(=O)C>[BrH:50].[BrH:50].[CH2:45]([O:44][C:42]([C@H:21]([NH:20][C@H:19]([C:18]([N:8]([CH:9]1[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)[CH2:7][C:6]([OH:49])=[O:5])=[O:48])[CH3:47])[CH2:22][CH2:23][CH2:24][CH2:25][CH:26]1[CH2:27][CH2:28][NH:29][CH2:30][CH2:31]1)=[O:43])[CH3:46]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 11765114HCID 11765114, compoundHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Product 1

HCID 18631453HCID 18631453, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 2 ml of acetic acid is dissolved 0.35 g of N-[N-[(R)-5-(1-benzyloxycarbonyl-4-piperidyl)-1-ethoxycarbonylpentyl]-L-alanyl]-N-(indan-2-yl)glycine 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 mixture, followed by shaking, and the supernatant layer is removed by decantation. The colorless precipitate is rinsed with ethyl ether and dried under reduced pressure to give 0.3 g of N-[N-[(R)-1-ethoxycarbonyl-5-(4-piperidyl)pentyl]-L-alanyl]-N-(indan-2-yl)glycine.dihydrobromide as a colorless powder.

Workup

  1. additionis added to the solution
  2. customthe supernatant layer is removed by decantation
  3. washThe colorless precipitate is rinsed with ethyl ether
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-c70a5fccd1374303a2312c7a773a00a2
Source dataset
uspto-grants-1989_03
Patent number
US04816466

Reaction notes

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