Hydrochloric Acid → HCID 69947202, compound

HRID 367252Notes

Reaction equation

HRID 367252 reaction equation
C([O:3][C:4]([C:6]1[C:7]([N:12]2[CH2:17][CH2:16][N:15]([CH2:18][CH2:19][CH:20]=[C:21]3[C:28]4[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=4[O:26][CH2:25][O:24][C:23]4[CH:33]=[CH:34][CH:35]=[CH:36][C:22]3=4)[CH2:14][CH2:13]2)=[N:8][CH:9]=[CH:10][CH:11]=1)=[O:5])C.[OH-].[Na+].[Cl:39]CCl.Cl>C(O)C>[ClH:39].[CH:29]1[C:28]2[C:21](=[CH:20][CH2:19][CH2:18][N:15]3[CH2:14][CH2:13][N:12]([C:7]4[C:6]([C:4]([OH:5])=[O:3])=[CH:11][CH:10]=[CH:9][N:8]=4)[CH2:17][CH2:16]3)[C:22]3[CH:36]=[CH:35][CH:34]=[CH:33][C:23]=3[O:24][CH2:25][O:26][C:27]=2[CH:32]=[CH:31][CH:30]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6344DichloromethaneHCID 14798Sodium HydroxideHCID 69949128HCID 69949128, compound

Product 1

HCID 69947202HCID 69947202, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of the above ester (0.99 g, 2 mmol) and 20% sodium hydroxide (1.5 ml) in ethanol (13 ml) was stirred at room temperature for 4 h. The mixture was poured into dichloromethane (100 ml), acidified with 2 N hydrochloric acid and washed with water (10 ml). The organic solution was dried (MgSO4) and activated charcoal was added. The mixture was stirred for 10 minutes, filtered and the solvent was removed in vacuo. The residue was triturated with acetone and the solid product was overlaid with ethyl acetate, stirred for 15 minutes, filtered off and washed with ethyl acetate. After drying, the title compound (0.80 g, 74%) was obtained.

Workup

  1. washwashed with water (10 ml)
  2. dry with materialThe organic solution was dried (MgSO4) and activated charcoal
  3. additionwas added
  4. stirringThe mixture was stirred for 10 minutes
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customThe residue was triturated with acetone
  8. stirringstirred for 15 minutes
  9. filtrationfiltered off
  10. washwashed with ethyl acetate
  11. customAfter drying

Sources & evidence

ORD record
ord-97ae71e4aaf642c8a4dc837adb11b951
Source dataset
uspto-grants-2000_10
Patent number
US06133268

Reaction notes

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