Lithium Hydroxide → HCID 59505429, compound

HRID 1253651Notes

Reaction equation

HRID 1253651 reaction equation
[Li+].[OH-].C[O:4][C:5]([C:7]1[CH:16]=[CH:15][C:14]2[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:17][C:18](=[O:26])[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:25])[C:9]=2[CH:8]=1)=[O:6]>CO.O>[Cl:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C:18]([NH:17][C@H:10]1[C:9]2[CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:16]=[CH:15][C:14]=2[CH2:13][CH2:12][CH2:11]1)=[O:26]

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 59505540HCID 59505540, compound

Product 1

HCID 59505429HCID 59505429, compoundYield 81.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

LiOH (4 equiv.) was added to a suspension of (8R)-8-[(2-chloro-benzoyl)amino]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester (B-06) in methanol and water and the reaction mixture was stirred at 25° C. for 2.5 hours. (According to TLC control: educt still present) The reaction mixture was topped up with 2 equiv. of LiOH and stirred at 25° C. overnight. Methanol was distilled off and the aqueous residue was diluted with ether and dist. water. The phases were separated and the aqueous phase was acidified with 1N HCl. Finally, the aqueous phase was extracted 4× with ethyl acetate (spot test) and the extract was dried over sodium sulfate and concentrated. Yield:81.4%.

Workup

  1. stirringstirred at 25° C. overnight
  2. distillationMethanol was distilled off
  3. additionthe aqueous residue was diluted with ether and dist
  4. customThe phases were separated
  5. extractionFinally, the aqueous phase was extracted 4× with ethyl acetate (spot test)
  6. dry with materialthe extract was dried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-abb7bed0c4904994ba573d711941fa73
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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