Argatroban (USAN:INN:BAN:JAN) → Argatroban

HRID 389071Notes

Reaction equation

HRID 389071 reaction equation
[CH3:1][C@H:2]1[CH2:7][C@H:6]([C:8]([OH:10])=[O:9])[N:5]([C:11]([C@@H:13]([NH:21][S:22]([C:25]2[C:30]3[NH:31][CH2:32][CH:33]([CH3:35])[CH2:34][C:29]=3[CH:28]=[CH:27][CH:26]=2)(=[O:24])=[O:23])[CH2:14][CH2:15][CH2:16][N:17]=[C:18]([NH2:20])[NH2:19])=[O:12])[CH2:4][CH2:3]1.O>O>[CH3:1][C@H:2]1[CH2:7][C@H:6]([C:8]([OH:10])=[O:9])[N:5]([C:11]([C@@H:13]([NH:21][S:22]([C:25]2[C:30]3[NH:31][CH2:32][CH:33]([CH3:35])[CH2:34][C:29]=3[CH:28]=[CH:27][CH:26]=2)(=[O:23])=[O:24])[CH2:14][CH2:15][CH2:16][N:17]=[C:18]([NH2:20])[NH2:19])=[O:12])[CH2:4][CH2:3]1

Participants

3

Reactant 1

HCID 92721Argatroban (USAN:INN:BAN:JAN)

Product 1

HCID 92722ArgatrobanYield 64.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
15 °C

Procedure

A jacketed glass reactor was fed with 100 ml of water and brought to 80° C.; 0.8 g of argatroban monohydrate was added at this temperature. The mass was maintained under stirring for 10 minutes at this temperature then the un-dissolved residue was removed by filtration. The mother liquors were quickly cooled to 15° C. (in about 2 minutes) and maintained at this temperature for 1 hour. The obtained solid was separated by filtration and dried at 80° C. at atmospheric pressure for 10 hours in a nitrogen flow, giving 0.5 g of argatroban anhydrous (HPLC purity=99.9%; isomer ratio=60.6:39.4; KF=0.26%). Yield 65%.

Workup

  1. custombrought to 80° C.
  2. temperatureThe mass was maintained
  3. customthe un-dissolved residue was removed by filtration
  4. temperaturemaintained at this temperature for 1 hour
  5. customThe obtained solid was separated by filtration
  6. customdried at 80° C. at atmospheric pressure for 10 hours in a nitrogen flow

Sources & evidence

ORD record
ord-6961d749250746a8990a241a26531ea7
Source dataset
uspto-grants-2013_02
Patent number
US08378106B2

Reaction notes

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