Lithium Hydroxide → HCID 20659563, compound

HRID 1371292Notes

Reaction equation

HRID 1371292 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): δ 8.36–8.33 (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-ac8b76f785e84110b7dfd51f2d757b6c
Source dataset
uspto-grants-2007_01
Patent number
US07157430B2

Reaction notes

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