Sulfuric Acid → HCID 69058084, compound

HRID 1869595Notes

Reaction equation

HRID 1869595 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[C:38]([NH2:45])=[C:37]([Cl:46])[CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:32][CH2:31][N:30]([CH3:33])[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:47]=[CH:48][CH:49]=[CH:50][C:4]=2[NH:3]1.[S:51](=[O:55])(=[O:54])([OH:53])[OH:52]>CO>[S:51]([OH:55])([OH:54])(=[O:53])=[O:52].[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:34][C:35]3[CH:40]=[C:39]([C:41]([F:43])([F:42])[F:44])[C:38]([NH2:45])=[C:37]([Cl:46])[CH:36]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:28][CH2:29][N:30]([CH3:33])[CH2:31][CH2:32]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:47]=[CH:48][CH:49]=[CH:50][C:4]=2[NH:3]1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 11629090HCID 11629090, compound

Product 1

HCID 69058084HCID 69058084, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

0.5 g (0.69 mmol) (R)-1-(4-amino-3-chloro-5-trifluoromethyl-benzyl)-2-[4-(4-methyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate are dissolved in 10 ml of methanol at ambient temperature. After the addition of 100 μl sulphuric acid (48% in water) the mixture is stirred for 3 hours at ambient temperature. After about 5 ml of methanol has been evaporated off, 1 ml of tert-butylmethylether is added, whereupon an oil is precipitated. After removal of the supernatant solvent the residue is combined with 5 ml acetone, during which time crystallisation sets in. The precipitate formed is filtered and dried for 12 hours at 30° C.

Workup

  1. customAfter about 5 ml of methanol has been evaporated off
  2. addition1 ml of tert-butylmethylether is added, whereupon an oil
  3. customis precipitated
  4. customAfter removal of the supernatant solvent the residue
  5. customis combined with 5 ml acetone, during which time crystallisation sets in
  6. customThe precipitate formed
  7. filtrationis filtered
  8. customdried for 12 hours at 30° C.

Sources & evidence

ORD record
ord-5e2c5c28ae374204b230dc38cfaa2f99
Source dataset
uspto-grants-2009_12
Patent number
US07638625B2

Reaction notes

Loading…