Acetate → HCID 130298492, compound

HRID 1087038Notes

Reaction equation

HRID 1087038 reaction equation
C([O-])(=O)C.[OH-].[Ba+2].[OH-].[NH2:8][CH:9]1[CH2:13][CH:12]([CH2:14][OH:15])[CH:11]=[CH:10]1.[C:16]([C@:24]([C:39]([OH:41])=[O:40])([OH:38])[C@:25]([C:30](=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)([OH:29])[C:26]([OH:28])=[O:27])(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>O.C(O)C.C(#N)C.C(O)(=O)C>[C:30]([C@:25]([C:26]([OH:28])=[O:27])([OH:29])[C@:24]([C:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([OH:38])[C:39]([OH:41])=[O:40])(=[O:37])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1.[NH2:8][C@@H:9]1[CH2:13][C@H:12]([CH2:14][OH:15])[CH:11]=[CH:10]1

Participants

9

Reactant 4

HCID 175AcetateHCID 6093286Barium hydroxideHCID 10313113(4-Aminocyclopent-2-en-1-yl)methanolHCID 12362977Di-benzoyl-d-tartaric acid

Product 1

HCID 130298492HCID 130298492, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

(±)-cis-4-Acetamidocyclopent-2-enemethyl acetate was hydrolyzed with barium hydroxide as in Example 1. The resulting syrup (acetic acid salt of (±)-4-amino-2-cyclopentene-1-methanol) was converted to free amine by stirring with an excess of Amberlite IRA-400 (OH-) resin in water. The resin was filtered off, washed with water, and the filtrate-wash evaporated to a pale yellow syrup which was dried by evaporation of portions of ethanol. Such a sample of amine (2.26 g, 20.0 mmol) and dibenzoyl-D-tartaric acid (Aldrich, 3.62 g, 10.0 mmol as 99%) were dissolved in hot absolute ethanol (35 mL). Refluxing acetonitrile (ca. 150 mL) was added to the cloud point and the solution was allowed to cool slowly to room temperature. The white needles which formed were recrystallized three times from the same solvent combination to give title compound as white plates (1.07 g, 37%); m.p. 160°-162°; [α]20D +66.9°, [α]20436 +165°, [α]20365 +325° (c=0.28, methanol). X-ray crystallography of this salt allowed the absolute configuration of the cation to be fixed by the known configuration of the D-dibenzoyl tartaric acid dianion. This salt crystallized in the space group C2 with one C6H12NO cation and one-half C18H14O8 dianion as the asymmetric unit.

Workup

  1. filtrationThe resin was filtered off
  2. washwashed with water
  3. customthe filtrate-wash evaporated to a pale yellow syrup which
  4. dry with materialwas dried by evaporation of portions of ethanol
  5. customThe white needles which formed
  6. customwere recrystallized three times from the same solvent combination

Sources & evidence

ORD record
ord-45d7651f845f43a59ec5bc2162e6994e
Source dataset
uspto-grants-1991_07
Patent number
US05034394

Reaction notes

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