Lithium Hydroxide → HCID 20659563, compound

HRID 1066048Notes

Reaction equation

HRID 1066048 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[C:14](=[O:27])[CH2:15][O:16][C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)=[O:4].[Li+].[OH-]>O1CCCC1>[C:17]1([O:16][CH2:15][C:14]([N:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH2:13][C@H:5]2[C:3]([OH:4])=[O:2])=[O:27])[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 69461737HCID 69461737, compound

Product 1

HCID 20659563HCID 20659563, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (2S)-N-[(1-naphthoxy)acetyl]indoline-2-carboxylic acid methyl ester (1.0 g, 2.77 mmol) in tetrahydrofuran (3.3 mL) at 0° C. was added 1.0 N LiOH solution (3.3 mL, 3.3 mmol). After stirring at 0° C. for 2 hours the mixture was concentrated, diluted with water, acidified to pH 3, and extracted with EtOAc. The EtOAc extract was washed with saturated NaCl, dried (Na2SO4), and evaporated to give the title compound (0.918 g, 96%) as an off-white solid. 1H NMR (CD3OD): δ8.36-8.33 (m, 1H), 8.15 (d, 1H, J=7.8 Hz), 7.81-7.78 (m, 1H), 7.49-7.18 (m, 7H), 7.10-7.04 (m, 1H), 6.92 (d, 1H, J=7.5 Hz), 5.32-4.94 (m, 5H), 3.69-3.34 (m, 2H).

Workup

  1. concentrationwas concentrated
  2. additiondiluted with water
  3. extractionextracted with EtOAc
  4. extractionThe EtOAc extract
  5. washwas washed with saturated NaCl
  6. dry with materialdried (Na2SO4)
  7. customevaporated

Sources & evidence

ORD record
ord-06aea8198b4f44dca364291f4feaa2ec
Source dataset
uspto-grants-2001_06
Patent number
US06242422B1

Reaction notes

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