1-Propanol → Sampatrilat

HRID 567942Notes

Reaction equation

HRID 567942 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].C(O)CC>C(#N)C>[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 10311-PropanolHCID 86756334HCID 86756334, compound

Product 1

HCID 6324648Sampatrilat

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

(S,S,S)-N-(1-[2-Carboxy-3-(N2-mesyllysylamino)propyl]-1-cyclopentylcarbonyl)tyrosine hydrate (the δ-form, see Preparation 2) (1.0 g) was stirred with either n-propanol or acetonitrile (10 ml) for 24 hours at room temperature. In each case the white solid obtained was collected by filtration and dried to provide the title compound, m.p. 172-176° C.

Workup

  1. customPreparation 2) (1.0 g)
  2. customIn each case the white solid obtained
  3. filtrationwas collected by filtration
  4. customdried

Sources & evidence

ORD record
ord-6b682b1f5ed94bd4b8562c1aa519786b
Source dataset
uspto-grants-2001_01
Patent number
US06180665B2

Reaction notes

Loading…