Hydrogen Bromide → HCID 59263887, compound

HRID 644983Notes

Reaction equation

HRID 644983 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:16]=[CH:15][C:14]([CH2:17][CH2:18][NH:19][CH2:20][CH2:21][C:22]([N:24]([CH:51]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[CH2:25][CH2:26][N:27]([CH2:38][CH2:39][C:40]2[C:48]3[S:47][C:46](=[O:49])[NH:45][C:44]=3[C:43]([OH:50])=[CH:42][CH:41]=2)C(=O)OCC2C=CC=CC=2)=[O:23])=[CH:13][CH:12]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br>ClCCl.C(O)(=O)C>[CH2:1]([NH:8][C:9](=[O:10])[C:11]1[CH:12]=[CH:13][C:14]([CH2:17][CH2:18][NH:19][CH2:20][CH2:21][C:22]([N:24]([CH:51]2[CH2:57][CH2:56][CH2:55][CH2:54][CH2:53][CH2:52]2)[CH2:25][CH2:26][NH:27][CH2:38][CH2:39][C:40]2[C:48]3[S:47][C:46](=[O:49])[NH:45][C:44]=3[C:43]([OH:50])=[CH:42][CH:41]=2)=[O:23])=[CH:15][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 59263913HCID 59263913, compound

Product 1

HCID 59263887HCID 59263887, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

The product from step iv) (0.106 g) was dissolved in dichloromethane (1.5 mL) and cooled to 0° C. Hydrobromic acid in acetic acid (33%, 0.6 mL) was added dropwise. The reaction mixture was stirred for 2 h then concentrated and azeotroped with toluene (×3) and methanol (×3). The crude material was purified by reverse phase HPLC (75-5% of 0.2% aqueous TFA in acetonitrile) to afford the product as a white solid (0.027 g).

Workup

  1. concentrationthen concentrated
  2. customazeotroped with toluene (×3) and methanol (×3)
  3. customThe crude material was purified by reverse phase HPLC (75-5% of 0.2% aqueous TFA in acetonitrile)

Sources & evidence

ORD record
ord-45d8b56902bb45dabc97114d260b8ad7
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

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