HCID 86756334, compound → Sampatrilat

HRID 567943Notes

Reaction equation

HRID 567943 reaction equation
O.[C:2]([C@H:5]([CH2:27][NH:28][C:29](=[O:41])[C@H:30]([CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH2:6][C:7]1([C:12]([NH:14][C@H:15]([C:24]([OH:26])=[O:25])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]1)([OH:4])=[O:3]>O.CC(C)=O>[C:2]([C@H:5]([CH2:27][NH:28][C:29](=[O:41])[C@H:30]([CH2:36][CH2:37][CH2:38][CH2:39][NH2:40])[NH:31][S:32]([CH3:35])(=[O:34])=[O:33])[CH2:6][C:7]1([C:12]([NH:14][C@H:15]([C:24]([OH:26])=[O:25])[CH2:16][C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)=[O:13])[CH2:11][CH2:10][CH2:9][CH2:8]1)([OH:4])=[O:3]

Participants

4

Reactant 1

HCID 86756334HCID 86756334, compound

Product 1

HCID 6324648Sampatrilat

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 962WaterSolvent

Procedure

(S,S,S)-N-(1-[2-Carboxy-3-(N2-mesyllysylamino)propyl]-1-cyclopentylcarbonyl)tyrosine hydrate (the δ-form, see Preparation 2) (847.0 g) was dissolved in water (762 ml) and the solution diluted with acetone (1.0 l). This solution was added slowly to vigorously stirred acetone (18.05 l) at room temperature and a white solid precipitated. The mixture was stirred at room temperature for 18 hours, the solid was collected by filtration, washed with acetone and dried to give the title compound as a white solid (775 g), m.p. 179-181° C. Found: C,53.42; H,6.88; N,9.37; S,5.49. C26H40N4O9S requires: C,53.41; H,6.90; N,9.58; S,5.48%.

Workup

  1. customPreparation 2) (847.0 g)
  2. customa white solid precipitated
  3. filtrationthe solid was collected by filtration
  4. washwashed with acetone
  5. customdried

Sources & evidence

ORD record
ord-2d8a21e2f32e4ae68eb74d02fae69bf1
Source dataset
uspto-grants-2001_01
Patent number
US06180665B2

Reaction notes

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