Diethyl Ether → 10-[4-((3r)-3-Hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-benzoyl]-10,11-dihydro-5h-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid methyl-pyridin-3-yl methyl-amide l-(+)-tartaric acid salt

HRID 1070485Notes

Reaction equation

HRID 1070485 reaction equation
[CH3:1][CH2:2][N:3]([C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[C:4]([C:6]1[N:15]2[C:9]([CH2:10][N:11]([C:20](=[O:36])[C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH2:32][CH2:31][CH2:30][C@@H:29]([OH:33])[C:28]=4[CH3:34])=[C:23]([CH3:35])[CH:22]=3)[C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[CH2:14]2)=[CH:8][CH:7]=1)=[O:5].C(OCC)C.[C:48]([OH:57])(=[O:56])[C@@H:49]([C@H:51]([C:53]([OH:55])=[O:54])[OH:52])[OH:50]>CO>[C:48]([OH:57])(=[O:56])[C@@H:49]([C@H:51]([C:53]([OH:55])=[O:54])[OH:52])[OH:50].[CH3:1][CH2:2][N:3]([C:37]1[CH:38]=[N:39][CH:40]=[CH:41][CH:42]=1)[C:4]([C:6]1[N:15]2[C:9]([CH2:10][N:11]([C:20](=[O:36])[C:21]3[CH:26]=[CH:25][C:24]([C:27]4[CH2:32][CH2:31][CH2:30][C@@H:29]([OH:33])[C:28]=4[CH3:34])=[C:23]([CH3:35])[CH:22]=3)[C:12]3[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=3[CH2:14]2)=[CH:8][CH:7]=1)=[O:5]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 444305L-Tartaric acidHCID 8658744610-[4-((3R)-3-Hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid methyl-pyridin-3-yl methyl-amide

Product 1

HCID 13172497710-[4-((3r)-3-Hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-benzoyl]-10,11-dihydro-5h-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid methyl-pyridin-3-yl methyl-amide l-(+)-tartaric acid saltYield 99.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10-[4-((3R)-3-Hydroxy-2-methyl-cyclohex-1-en-1-yl)-3-methyl-benzoyl]-10,11-dihydro-5H-pyrrolo[2,1-c][1,4]benzodiazepine-3-carboxylic acid methyl-pyridin-3-yl methyl-amide (0.120 g, 0.214 mmol) of Example 3, was dissolved in boiling diethyl ether. A solution of L-(+)-tartaric acid (0.0320 g, 0.214 mmol) in hot methanol (1 mL) was added, the mixture cooled and solvent evaporated. Diethyl ether was added to the residue causing a white solid to form which was filtered and dried in vacuo to afford 0.152 g of the title compound as the tartaric acid salt.

Workup

  1. temperaturethe mixture cooled
  2. customsolvent evaporated
  3. additionDiethyl ether was added to the residue
  4. customto form which
  5. filtrationwas filtered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-719cb718b1e74f00a136f28443a2bb61
Source dataset
uspto-grants-2005_06
Patent number
US06903087B2

Reaction notes

Loading…