Lithium Hydroxide → HCID 86638397, compound

HRID 545566Notes

Reaction equation

HRID 545566 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[C:27](F)[CH:26]=3)[C:10]3[CH2:11][CH2:12][C@@H:13]([NH:18][C:19](=[O:23])[CH:20]([CH3:22])[CH3:21])[CH2:14][C:15]=3[C:16]=2[CH:17]=1)=[O:4].[Li+].[OH-]>>[CH2:24]([N:9]1[C:8]2[CH:7]=[CH:6][C:5]([C:3]([OH:4])=[O:2])=[CH:17][C:16]=2[C:15]2[CH2:14][CH:13]([NH:18][C:19](=[O:23])[CH:20]([CH3:21])[CH3:22])[CH2:12][CH2:11][C:10]1=2)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 3939Lithium HydroxideHCID 57431679HCID 57431679, compound

Product 1

HCID 86638397HCID 86638397, compoundYield 100.1%

Conditions

Temperature
70 °C

Procedure

Add (R)-9-(3-fluorobenzyl)-6-isobutyrylamino-6,7,8,9-tetrahydro-5H-carbazole-3-carboxylic acid methyl ester (2.54 g, 6.01 mmol) to a solution of excess LiOH in methanol/water/TBF (33:33:33) and stir for 24 h at 70° C. Concentrate in vacuo, partition between water and EtOAc/Et2O. Make the aqueous layer acidic with aqueous HCl and extract with EtOAc. Wash with brine, filter the solids from the EtOAc layer and slurry in hot EtOAc. Collect by filtration and dry to give 2.35 g (96%) of a white solid. MS (ES): m/z 409 (M+1), HPLC: Rt=1.93 (100%).

Workup

  1. concentrationConcentrate in vacuo
  2. custompartition between water and EtOAc/Et2O
  3. extractionextract with EtOAc
  4. washWash with brine
  5. filtrationfilter the solids from the EtOAc layer and slurry in hot EtOAc
  6. filtrationCollect by filtration
  7. customdry

Sources & evidence

ORD record
ord-c69ca849f64b4e9a97c47d4442fae9cc
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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