Hydrogen Bromide → HCID 14128423, compound

HRID 569688Notes

Reaction equation

HRID 569688 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]2[C:3]=1[C:4](=[O:84])[C:5]1[C:6]([NH:51][CH2:52][CH2:53][NH:54][C:55](=[O:83])[C@H:56]([CH2:79][CH:80]([CH3:82])[CH3:81])[NH:57][C:58](=[O:78])[C@H:59]([CH2:71][C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)[NH:60]C(OCC3C=CC=CC=3)=O)=[CH:7][CH:8]=[C:9]([NH:18][CH2:19][CH2:20][NH:21][C:22](=[O:50])[C@H:23]([CH2:46][CH:47]([CH3:49])[CH3:48])[NH:24][C:25](=[O:45])[C@H:26]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[NH:27]C(OCC3C=CC=CC=3)=O)[C:10]=1[C:11]2=[O:17].[BrH:85]>C(O)(=O)C>[BrH:85].[BrH:85].[OH:1][C:2]1[CH:15]=[CH:14][C:13]([OH:16])=[C:12]2[C:3]=1[C:4](=[O:84])[C:5]1[C:6]([NH:51][CH2:52][CH2:53][NH:54][C:55](=[O:83])[C@H:56]([CH2:79][CH:80]([CH3:82])[CH3:81])[NH:57][C:58](=[O:78])[C@H:59]([CH2:71][C:72]3[CH:77]=[CH:76][CH:75]=[CH:74][CH:73]=3)[NH2:60])=[CH:7][CH:8]=[C:9]([NH:18][CH2:19][CH2:20][NH:21][C:22](=[O:50])[C@H:23]([CH2:46][CH:47]([CH3:49])[CH3:48])[NH:24][C:25](=[O:45])[C@H:26]([CH2:38][C:39]3[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=3)[NH2:27])[C:10]=1[C:11]2=[O:17]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 16166611HCID 16166611, compound

Product 1

HCID 14128423HCID 14128423, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A 2.75 g portion of N,N'-[(9,10-dihydro-5,8-dihydroxy-9,10-dioxo-1,4-anthracenediyl)bis(imino-2,1-ethanediyl)]bis[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl-L-leucinamide] was reacted by a modification of the procedure of Example 31, by being dissolved in 75 ml of glacial acetic acid previously saturated for 5 minutes with anhydrous hydrogen bromide. The mixture was reacted for 2.5 hours, then more hydrogen bromide was bubbled into the solution for 15 minutes and after another 2 hours the solid was collected, giving 2.7 g of the desired product, mp 180° C. (dec.).

Workup

  1. customThe mixture was reacted for 2.5 hours
  2. custommore hydrogen bromide was bubbled into the solution for 15 minutes and after another 2 hours the solid
  3. customwas collected

Sources & evidence

ORD record
ord-f4794b6d866b4959a1f191b84c4dd2a6
Source dataset
uspto-grants-1988_03
Patent number
US04732970

Reaction notes

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