Hydrogen Bromide → HCID 13201335, compound

HRID 1632380Notes

Reaction equation

HRID 1632380 reaction equation
C([O:5][C:6](=[O:51])[CH2:7][N:8]([C:18](=[O:50])[C@H:19]([CH2:35][CH2:36][CH2:37][CH2:38][NH:39]C(OCC1C=CC=CC=1)=O)[NH:20][C@@H:21]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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:52].CCOCC>C(O)(=O)C>[BrH:52].[BrH:52].[CH2:33]([O:32][C:30]([C@H:21]([NH:20][C@H:19]([C:18]([N:8]([CH:9]1[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17]1)[CH2:7][C:6]([OH:51])=[O:5])=[O:50])[CH2:35][CH2:36][CH2:37][CH2:38][NH2:39])[CH2:22][CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 13132322HCID 13132322, compound

Product 1

HCID 13201335HCID 13201335, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

Nα -[1-(R)-Ethoxycarbonyl-3-phenylpropyl]-Nε -carbobenzoxy-L-lysyl-N-(indan-2-yl)glycine tert-butyl ester (1 g) is dissolved in 2 ml of acetic acid. To the solution, 8 ml of 25% hydrobromic acid solution in acetic acid is added, and the mixture is allowed to stand at room temperature for 30 minutes. On adding 200 ml of ether and 100 ml of petroleum ether to the reaction mixture, a crystalline precipitate forms. This is collected by filtration and recrystallized from a mixture of methanol and ethyl ether to give 0.8 g of Nα -[1-(R)-ethoxycarbonyl-3-phenylpropyl]-L-lysyl-N-(indan-2-yl)glycine dihydrobromide melting at 128°-133° C. with decomposition.

Workup

  1. filtrationThis is collected by filtration
  2. customrecrystallized from a mixture of methanol and ethyl ether

Sources & evidence

ORD record
ord-377c2fcedf1f438c96a189c949585446
Source dataset
uspto-grants-1984_10
Patent number
US04474692

Reaction notes

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