Toluene → HCID 67319046, compound

HRID 644975Notes

Reaction equation

HRID 644975 reaction equation
[CH:1]1([N:7]([C:34](=[O:48])[CH2:35][CH2:36][NH:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:41]=2[F:47])[CH2:8][CH2:9][N:10]([CH2:21][CH2:22][C:23]2[C:31]3[S:30][C:29](=[O:32])[NH:28][C:27]=3[C:26]([OH:33])=[CH:25][CH:24]=2)C(=O)OCC2C=CC=CC=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[BrH:49].C(O)(=O)C.C1(C)C=CC=CC=1>C(O)(=O)C>[BrH:49].[BrH:49].[CH:1]1([N:7]([CH2:8][CH2:9][NH:10][CH2:21][CH2:22][C:23]2[C:31]3[S:30][C:29](=[O:32])[NH:28][C:27]=3[C:26]([OH:33])=[CH:25][CH:24]=2)[C:34](=[O:48])[CH2:35][CH2:36][NH:37][CH2:38][CH2:39][C:40]2[CH:45]=[CH:44][CH:43]=[C:42]([F:46])[C:41]=2[F:47])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 59263935HCID 59263935, compound

Product 1

HCID 67319046HCID 67319046, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of the carbamate from step (i) (0.4 g) in acetic acid (2 mL) was treated with hydrogen bromide/acetic acid (33%, 2 mL) and stirred for 1 h. Toluene (10 mL) was added, the mixture was evaporated in vacuo, the residue purified by reverse phase HPLC with 0.2% aqueous TFA/acetonitrile as eluent and the pure fractions evaporated in vacuo. The solid residue was dissolved in a mixture of ethanol (5 mL) and acetonitrile (15 mL) and treated with hydrobromic acid in aqueous acetonitrile (16%, 1.8 mL). A solid gradually precipitated and was filtered off, washed with acetonitrile and slurried in ethanol. The solid was filtered off, washed with a little ethanol and dried to afford the title product (0.036 g) as a white solid.

Workup

  1. customthe mixture was evaporated in vacuo
  2. customthe residue purified by reverse phase HPLC with 0.2% aqueous TFA/acetonitrile as eluent
  3. customthe pure fractions evaporated in vacuo
  4. dissolutionThe solid residue was dissolved in a mixture of ethanol (5 mL) and acetonitrile (15 mL)
  5. additiontreated with hydrobromic acid in aqueous acetonitrile (16%, 1.8 mL)
  6. customA solid gradually precipitated
  7. filtrationwas filtered off
  8. washwashed with acetonitrile
  9. filtrationThe solid was filtered off
  10. washwashed with a little ethanol
  11. customdried

Sources & evidence

ORD record
ord-8d62ad9a530d40698fff8ad4051b6b24
Source dataset
uspto-grants-2010_04
Patent number
US07700782B2

Reaction notes

Loading…