Water → HCID 59505298, compound

HRID 1253652Notes

Reaction equation

HRID 1253652 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].O>CO>[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 3

HCID 962WaterHCID 3939Lithium Hydroxide2×HCID 59505254HCID 59505254, compound

Product 1

HCID 59505298HCID 59505298, compoundYield 84.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

LiOH (6 equiv.) was added to a suspension of (8S)-8-[(2-chloro-benzoyl)amino]-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid methyl ester (B-07) in methanol and water and the reaction mixture was stirred at 25° C. for 4 hours. (According to TLC control: educt still present). The reaction mixture was topped up with 1 equiv. of LiOH and stirred at 25° C. for 1 hour. 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: 84.8%

Workup

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

Sources & evidence

ORD record
ord-56118db805d24d37bd479c2e95742a00
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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