Methanol--water (1/1) → Sampatrilat

HRID 567937Notes

Reaction equation

HRID 567937 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.CO>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 2

HCID 22242641Methanol--water (1/1)HCID 86756334HCID 86756334, compound

Product 1

HCID 6324648Sampatrilat

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

A solution of (S,S,S)-N-(1-[2-carboxy-3-(N2-mesyllysylamino)propyl]-1-cyclopentylcarbonyl)tyrosine hydrate (the δ-form, see Preparation 2) (3.0 g) in a 1:5 water/methanol mixture (18 ml) or a 1:10 water/acetone mixture (33 ml) was stirred for 3 days at room temperature. The resulting solid was collected by filtration and dried to give the title compound as a white solid, m.p. 246-8° C. (from the aqueous methanol method), m.p. 242-3° C. (from the aqueous acetone method).

Workup

  1. filtrationThe resulting solid was collected by filtration
  2. customdried

Sources & evidence

ORD record
ord-57ef9b6841144023a53b877130960543
Source dataset
uspto-grants-2001_01
Patent number
US06180665B2

Reaction notes

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