Lithium Hydroxide → (3R)-3-{[(tert-butoxy)carbonyl]amino}-2,3-dihydro-1H-indene-5-carboxylic acid

HRID 1193417Notes

Reaction equation

HRID 1193417 reaction equation
[Li+].[OH-].[C:3]([O:7][C:8]([NH:10][C@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([O:22]C)=[O:21])[CH:18]=2)[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O.CO.C1COCC1>[C:3]([O:7][C:8]([NH:10][C@H:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]([OH:22])=[O:21])[CH:18]=2)[CH2:13][CH2:12]1)=[O:9])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59505324Methyl (R)-3-((tert-butoxycarbonyl)amino)-2,3-dihydro-1H-indene-5-carboxylate

Product 1

HCID 66798654(3R)-3-{[(tert-butoxy)carbonyl]amino}-2,3-dihydro-1H-indene-5-carboxylic acidYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

LiOH (647 mg, 15.42 mmol, 3 eq), dissolved in water (8 ml), was added dropwise to an ice-cooled (0° C.) solution of (R)-methyl 3-(tert-butoxycarbonylamino)-2,3-dihydro-1H-indene-5-carboxylate (stage (ii) product of A-07) (1.5 g, 5.15 mmol, 1 eq) in MeOH:THF (1:1, 16 ml), and stirring was carried out for 6 h at RT. After monitoring by thin-layer chromatography, the reaction solution was concentrated and the residue was taken up in water (20 ml) and adjusted to pH 3 with NaHSO3. The acidic, aqueous phase was extracted with ethyl acetate (2×150 ml), washed with sat. NaCl solution (2×50 ml), dried over sodium sulfate and concentrated under reduced pressure. Yield: 70% (1.0 g, 3.61 mmol).

Workup

  1. concentrationthe reaction solution was concentrated
  2. extractionThe acidic, aqueous phase was extracted with ethyl acetate (2×150 ml)
  3. washwashed with sat. NaCl solution (2×50 ml)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-aaf990aa573a490881a61b0f43e2276e
Source dataset
uspto-grants-2014_03
Patent number
US08680159B2

Reaction notes

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