Lithium Hydroxide → HCID 71209270, compound

HRID 1912624Notes

Reaction equation

HRID 1912624 reaction equation
[C:1]([O:5][C@@H:6]([C:11]1[C:12]([C:30]2[CH:31]=[CH:32][C:33]3[O:37][CH2:36][CH2:35][C:34]=3[CH:38]=2)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([O:9]C)=[O:8])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-]>CO.C1COCC1.O>[C:1]([O:5][C@@H:6]([C:11]1[C:12]([C:30]2[CH:31]=[CH:32][C:33]3[O:37][CH2:36][CH2:35][C:34]=3[CH:38]=2)=[C:13]2[CH:20]=[CH:19][N:18]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=3)[C:14]2=[N:15][C:16]=1[CH3:17])[C:7]([OH:9])=[O:8])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 71209239HCID 71209239, compound

Product 1

HCID 71209270HCID 71209270, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 21892291Methanol tetrahydrofuran waterSolvent

Conditions

Temperature
70 °C

Procedure

A solution of (S)-methyl 2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-(2,3-dihydrobenzofuran-5-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetate (126 mg, 0.242 mmol) in MeOH/THF/water=2/2/1 (10 mL) was treated with LiOH (110 mg, 4.59 mmol) and the mixture was heated at 70° C. until the reaction was judged complete. The mixture was concentrated, water was added and then adjusted to pH 2 with 1N HCl. The mixture was extracted with ethyl acetate. The extracts were washed with brine, dried over Na2SO4, filtered and concentrated to afford (S)-2-(tert-butoxy)-2-(1-(3,4-difluorobenzyl)-4-(2,3-dihydrobenzofuran-5-yl)-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)acetic acid (105 mg, 0.207 mmol, 86% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.62-7.47 (m, 1 H), 7.39-7.27 (m, 1 H), 7.16-7.05 (m, 2 H), 7.05-6.96 (m, 2 H), 6.92 (dd, J=4.7, 8.2 Hz, 1 H), 6.30-6.16 (m, 1 H), 5.64-5.54 (m, 1 H), 5.51-5.43 (m, 1 H), 5.43-5.33 (m, 1 H), 4.67 (td, J=4.2, 8.7 Hz, 2 H), 3.41-3.20 (m, 2 H), 2.70 (s, 3H), 0.99-0.89 (s, 9 H); LC/MS ES+=507.35 (M+1).

Workup

  1. concentrationThe mixture was concentrated
  2. additionwater was added
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-36b284fa2b5143408d4b759f79683396
Source dataset
uspto-grants-2013_12
Patent number
US08609653B2

Reaction notes

Loading…