Hydrochloric Acid → N-ethyl 2,3-dihydroxycyclopentane carboxamide dihydrochloride hydrate
Reaction equation
[ClH:1].[CH2:2]([NH:4][C:5]([CH:7]1[CH2:11][CH2:10][CH:9]([OH:12])[CH:8]1[OH:13])=[O:6])[CH3:3]>>[OH2:6].[ClH:1].[ClH:1].[CH2:2]([NH:4][C:5]([CH:7]1[CH2:11][CH2:10][CH:9]([OH:12])[CH:8]1[OH:13])=[O:6])[CH3:3]Participants
Procedure
The zinc metal and any other insoluble impurities are then removed by filtration of the contents of vessel and the filtrate is collected in another reaction vessel. Acid hydrolysis of [3aR-[3aα,4α,6a(R*),6aα]]-6-[4-[[1-[(3-chlorothien-2-yl)methyl]propyl]amino]-3-aminopyrid-2-ylamino] N-ethyl tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide (XIII) is then effected by adding concentrated HCl to the second reaction vessel and heating until conversion to [1S-[1α,2β,3β,4α(S*)]]-4-[3-amino-4-[[1-[3-chlorothien-2-yl)methyl]propyl]amino]pyrid-2-ylamino] N-ethyl 2,3-dihydroxycyclopentanecarboxamide (XIII) is essentially complete. Cooling of the second reaction vessel results in crystallization of [1S-[1α,2β,3β,4α(S*)]]-4-[3-amino-4-[[1-[3-chlorothien-2-yl)methyl]propyl]amino]pyrid-2-ylamino] N-ethyl 2,3-dihydroxycyclopentane carboxamide dihydrochloride hydrate which is isolated by filtration.
Workup
- customThe zinc metal and any other insoluble impurities are then removed by filtration of the contents of vessel
- customthe filtrate is collected in another reaction vessel
- customAcid hydrolysis of [3aR-[3aα,4α,6a(R*),6aα]]-6-[4-[[1-[(3-chlorothien-2-yl)methyl]propyl]amino]-3-aminopyrid-2-ylamino] N-ethyl tetrahydro-2,2-dimethyl-4H-cyclopenta-1,3-dioxole-4-carboxamide (XIII)
- temperatureCooling of the second reaction vessel
Sources & evidence
- ORD record
- ord-551bfe40c7de47a080ca8d466a9656aa
- Source dataset
- uspto-grants-2001_02
- Patent number
- US06184382B2
Reaction notes
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