Methanol → 5-Benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetic acid

HRID 1649945Notes

Reaction equation

HRID 1649945 reaction equation
[C:1]([NH:9][CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[C:15]([O:20][CH2:21][C:22]([O:24]C)=[O:23])=[CH:14][CH:13]=[CH:12][C:11]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>[OH-].[Na+]>[C:1]([NH:9][CH:10]1[CH2:19][CH2:18][CH2:17][C:16]2[C:15]([O:20][CH2:21][C:22]([OH:24])=[O:23])=[CH:14][CH:13]=[CH:12][C:11]1=2)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887Methanol2×HCID 14014967Methyl 5-benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetate

Product 1

HCID 198554765-Benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetic acid

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

50 mmol of methyl 5-benzoylamino-5,6,7,8-tetrahydro-naphth-1-yl-oxyacetate are stirred in 60 ml of 1N NaOH and 120 ml of MeOH at room temperature for 6 hours. The methanol is stripped off, the NaOH solution is extracted by shaking with ethyl acetate and the extract is then acidified with 10% strength HCl solution. The acid solution is extracted by shaking 3 times with ethyl acetate or tetrahydrofuran, the extract is dried over Na2SO4 and evaporated and the residue is dried under a high vacuum.

Workup

  1. extractionthe NaOH solution is extracted
  2. extractionThe acid solution is extracted
  3. stirringby shaking 3 times with ethyl acetate or tetrahydrofuran
  4. dry with materialthe extract is dried over Na2SO4
  5. customevaporated
  6. customthe residue is dried under a high vacuum

Sources & evidence

ORD record
ord-cb347fb98a1b402f985bd63619970d7a
Source dataset
uspto-grants-1990_05
Patent number
US04921998

Reaction notes

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