2,3-Dihydroxybutanedioic Acid → HCID 20060592, compound

HRID 1723445Notes

Reaction equation

HRID 1723445 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][CH:12]1[CH2:17][CH2:16][N:15]([CH2:18][CH:19]([CH2:21][O:22][C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[OH:20])[CH2:14][CH2:13]1.[OH:30][CH:31]([CH:35]([OH:39])[C:36]([OH:38])=[O:37])[C:32]([OH:34])=[O:33]>C(O)C>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][NH:11][CH:12]1[CH2:13][CH2:14][N:15]([CH2:18][CH:19]([CH2:21][O:22][C:23]2[CH:24]=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[OH:20])[CH2:16][CH2:17]1.[OH:30][CH:31]([CH:35]([OH:39])[C:36]([O-:38])=[O:37])[C:32]([O-:34])=[O:33]

Participants

5

Reactant 2

HCID 8752,3-Dihydroxybutanedioic AcidHCID 20060592HCID 20060592, compound

Product 2

HCID 38061142,3-DihydroxybutanedioateHCID 20060592HCID 20060592, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred solution of 5 parts of 4-[(2-benzothiazolyl)methylamino]-α-[(4-fluorophenoxy)methyl]-1-piperidineethanol in 80 parts of ethanol were added 1.8 parts of (+)-[R-(R*,R*)]-2,3-dihydroxybutanedioic acid while boiling. The product was allowed to crystallize. It was filtered off and dried, yielding 5.5 parts (94%) of (+)-4-[(2-benzothiazolyl)methylamino]-α-[(4-fluorophenoxy)methyl]-1-piperidineethanol [R-(R*,R*)]-2,3-dihydroxybutanedioate (2:1); mp. 189.1° C. (457).

Workup

  1. customto crystallize
  2. filtrationIt was filtered off
  3. customdried

Sources & evidence

ORD record
ord-f95868137c524532aa42c885e50743f8
Source dataset
uspto-grants-1989_08
Patent number
US04861785

Reaction notes

Loading…