Hydrogen Bromide → HCID 22945653, compound

HRID 1782748Notes

Reaction equation

HRID 1782748 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][NH:13][C:14]([NH:16][C@@H:17]([C:28]([NH:30][C@H:31]([C:47]([N:49]1[CH2:54][CH2:53][N:52]([C:55]2[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=2)[CH2:51][CH2:50]1)=[O:48])[CH2:32][CH2:33][CH2:34][CH2:35][NH:36]C(OCC1C=CC=CC=1)=O)=[O:29])[CH2:18][C:19]1[CH:24]=[C:23]([Br:25])[C:22]([OH:26])=[C:21]([Br:27])[CH:20]=1)=[O:15].Br.C(OCC)C>C(O)(=O)C.C1(OC)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][CH2:12][NH:13][C:14]([NH:16][CH:17]([C:28]([NH:30][C@H:31]([C:47]([N:49]1[CH2:50][CH2:51][N:52]([C:55]2[CH:60]=[CH:59][N:58]=[CH:57][CH:56]=2)[CH2:53][CH2:54]1)=[O:48])[CH2:32][CH2:33][CH2:34][CH2:35][NH2:36])=[O:29])[CH2:18][C:19]1[CH:24]=[C:23]([Br:25])[C:22]([OH:26])=[C:21]([Br:27])[CH:20]=1)=[O:15]

Participants

6

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 53647247HCID 53647247, compound

Product 1

HCID 22945653HCID 22945653, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolvent2×HCID 7519AnisoleSolvent

Procedure

A mixture of 0.8 g (0.84 mmol) of 1-[N2—[N-[[[2-(2,5-dimethoxyphenyl)ethyl]amino]carbonyl]-3,5-dibromo-D-tyrosyl]-N6-[(phenylmethoxy)carbonyl]-L-lysyl]-4-(4-pyridinyl)-piperazine, 50 ml of glacial acetic acid, 25 ml of a 33% solution of hydrogen bromide in glacial acetic acid and 2 ml of anisole was stirred for 12 hours at ambient temperature. The reaction mixture was stirred into diethylether and the resulting precipitate was suction filtered. The solid residue was purified by column chromatography (MN-silica gel 60, Macherey-Nagel, 70-230 mesh ASTM, eluant:ethyl acetate/methanol/conc. aqueous ammonia=8/2/0.2 (v/v/v)). 0.3 g (44% of theory) of the desired product was obtained as an amorphous solid.

Workup

  1. filtrationfiltered
  2. customThe solid residue was purified by column chromatography (MN-silica gel 60, Macherey-Nagel, 70-230 mesh ASTM, eluant:ethyl acetate/methanol/conc. aqueous ammonia=8/2/0.2 (v/v/v))

Sources & evidence

ORD record
ord-6bc6d39ce0d2490a84430efd397273ce
Source dataset
uspto-grants-2009_03
Patent number
US07498325B2

Reaction notes

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