3-Mercaptopropionic Acid → HCID 67779970, compound

HRID 2400195Notes

Reaction equation

HRID 2400195 reaction equation
[OH:1][C:2]1[C:7]([CH2:8][CH2:9][CH3:10])=[C:6]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22](O)[CH2:23][CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:18][CH:17]=2)[CH:5]=[CH:4][C:3]=1[C:33](=[O:35])[CH3:34].[SH:36][CH2:37][CH2:38][C:39]([OH:41])=[O:40].CCOC(C)=O.[OH-].[Na+:49]>ClCCCl.CC(O)=O.CCO>[Na+:49].[C:33]([C:3]1[CH:4]=[CH:5][C:6]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH:22]([S:36][CH2:37][CH2:38][C:39]([O-:41])=[O:40])[CH2:23][CH2:24][CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)=[CH:18][CH:17]=2)=[C:7]([CH2:8][CH2:9][CH3:10])[C:2]=1[OH:1])(=[O:35])[CH3:34]

Participants

8

Reactant 4

HCID 65143-Mercaptopropionic AcidHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 19382486HCID 19382486, compound

Product 1

HCID 67779970HCID 67779970, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 111,2-DichloroethaneSolventHCID 702EthanolSolvent

Procedure

To a 0° C. solution of the alcohol from Step 2 (275 mg) and 3-mercaptopropionic acid (64 mg) in 1,2-dichloroethane (10 mL) was added BF3 ·OEt2 (355 mg). After 1 hr. at 0° C., the reaction mixture was poured on 25% aqueous NH4OAc containing AcOH (3 drops) and EtOAc. The organic layer was separated and the aqueous further extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine, dried with MgSO4 and solvents were removed under reduced pressure to yield an oil which was spectroscopically pure. The oil was dissolved in EtOH and 2N NaOH (1 equivalent) was added. Ethanol was removed under reduced pressure and the residue was dissolved in H2 0 and freeze dried to yield the title compound as a hemihydrate.

Workup

  1. customThe organic layer was separated
  2. extractionthe aqueous further extracted with EtOAc (2×10 mL)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried with MgSO4 and solvents
  5. customwere removed under reduced pressure
  6. customto yield an oil which
  7. customEthanol was removed under reduced pressure
  8. dissolutionthe residue was dissolved in H2 0
  9. customfreeze dried

Sources & evidence

ORD record
ord-508c7b18612349509cb84df9643a560f
Source dataset
uspto-grants-1995_09
Patent number
US05453443

Reaction notes

Loading…