Hydrochloric Acid → HCID 67723267, compound

HRID 1682548Notes

Reaction equation

HRID 1682548 reaction equation
C([O:3][C:4]([C@@H:6]1[CH2:11][CH2:10][CH2:9][N:8]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH2:7]1)=[O:5])C.[OH-].[Na+].Cl.[Cl:31]CCl>C(O)C.CC(C)=O>[ClH:31].[CH2:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[O:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:6]([C:4]([OH:5])=[O:3])[CH2:7]1)[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 54005589HCID 54005589, compound

Product 1

HCID 67723267HCID 67723267, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 702EthanolSolvent

Procedure

The above ester (1.7 g, 4.6 mmol) was dissolved in ethanol (10 ml) and 4N sodium hydroxide (3.5 ml) was added. The mixture was stirred at ambient temperature for 5 h. Excess concentrated hydrochloric acid was added followed by dichloromethane (300 ml). The phases were separated and the organic phase was dried (Na2SO4). The solvent was evaporated in vacuo to give a foamy residue which was dissolved in acetone (15 ml). The solid which formed was isolated by filtration and dried to give 1.3 g of the title compound as a solid.

Workup

  1. customThe phases were separated
  2. dry with materialthe organic phase was dried (Na2SO4)
  3. customThe solvent was evaporated in vacuo
  4. customto give a foamy residue which
  5. customThe solid which formed
  6. customwas isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-d418ba92cb2b4e0880d2eec3b3836a05
Source dataset
uspto-grants-1997_06
Patent number
US05635518

Reaction notes

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