Hydrochloric Acid → HCID 59006941, compound

HRID 1174534Notes

Reaction equation

HRID 1174534 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:11]3[C:16]([C@@H:17]4[C@H:22]([N:23]=2)[CH2:21][CH2:20][O:19][CH2:18]4)=[CH:15][C:14]([O:24][CH2:25][CH3:26])=[C:13]([O:27][CH3:28])[CH:12]=3)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>O1CCOCC1.O>[CH2:25]([O:24][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][C:13]=1[O:27][CH3:28])[C:10]([C:7]1[CH:6]=[CH:5][C:4]([C:3]([OH:29])=[O:2])=[CH:9][CH:8]=1)=[N:23][C@H:22]1[C@@H:17]2[CH2:18][O:19][CH2:20][CH2:21]1)[CH3:26]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59006940HCID 59006940, compound

Product 1

HCID 59006941HCID 59006941, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 7.6 mmol of 4((4aR,10aR)-6-Ethoxy-7-methoxy-1,4,4a,10a-tetrahydro-2H-3-oxa-10-aza-phenanthren-9-yl)-benzoic acid methyl ester in 100 ml of dioxan a solution of 7.5 ml of 2 molar sodium hydroxide in water is added and the mixture is stirred for 15 h at RT. A solution of 7.5 ml of 2 molar HCl in water is added and the mixture is stirred for 30 min. After concentration under reduced pressure the solid residue is treated with 100 ml of dichloromethane. After filtering the filtrate is concentrated under reduced pressure yielding the title compound as a grayish solid residue. The title compound is stirred up with diethylether, filtered off and dried under reduced pressure yielding the title compound as white powdery solid. M.p. 203-205° C.

Workup

  1. stirringthe mixture is stirred for 30 min
  2. concentrationAfter concentration under reduced pressure the solid residue
  3. additionis treated with 100 ml of dichloromethane
  4. filtrationAfter filtering the filtrate
  5. concentrationis concentrated under reduced pressure

Sources & evidence

ORD record
ord-eb690f69a9b446e881aeba051a4ff04d
Source dataset
uspto-grants-2010_11
Patent number
US07838521B2

Reaction notes

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