Lithium Hydroxide → HCID 9907777, compound

HRID 567345Notes

Reaction equation

HRID 567345 reaction equation
[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH:16]([C:21](=[O:23])[NH2:22])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][C:13]=2[O:24][CH2:25][C:26]([O:28]C)=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CO>[CH2:1]([N:8]1[C:20]2[CH2:19][CH2:18][CH2:17][CH:16]([C:21](=[O:23])[NH2:22])[C:15]=2[C:14]2[C:9]1=[CH:10][CH:11]=[CH:12][C:13]=2[O:24][CH2:25][C:26]([OH:28])=[O:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 3939Lithium Hydroxide2×HCID 86756279HCID 86756279, compound

Product 1

HCID 9907777HCID 9907777, compoundYield 86.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 30 mg (0.076 mmol) of [9-benzyl-4-carbamoyl-1,2,3,4-tetrahydrocarbazole-5-yl]oxyacetic acid, methyl ester in 1.0 mL of THF and 1.0 mL of MeOH was treated with 0.2 mL of 1 N aqueous LiOH (0.2 mmol). The mixture was stirred for 18 hours. An additional 0.2 mL of 1 N aqueous LiOH (0.2 mmol) was added and stirring continued. After 1 hour, the mixture was concentrated in vacuo. The residue was dissolved in 2.0 mL of H2O and the solution acidified with 0.2 N aqueous HCl. The solid was filtered and dried to afford 25 mg of [9-benzyl-4-carbamoyl-1,2,3,4-tetrahydrocarbazole-5-yl]oxyacetic acid as a white solid. 1H NMR (DMSO-d6) δ 7.36-7.12 (m, 5H), 7.05-6.83 (m, 5H), 6.71 (br s, 1H), 6.35 (d, 1H, J=7.6 Hz), 5.27 (s, 2H), 4.64 (s, 2H), 3.93-3.84 (m, 2H), 2.75-2.64 (m, 1H), 2.16-1.95 (m, 2H), 1.81-1.64 (m, 2H) and 1 proton masked by H2O peak between 2.58-2.40. IR (KBr, cm−1) 3435, 2936, 1722, 1644, 1586, 1566, 1495, 1451, 1354, 1227, 1134, 730, 716, and 698. MS (ES) m/e 377 (M−1) and 379 (M+1).

Workup

  1. stirringstirring
  2. waitAfter 1 hour
  3. concentrationthe mixture was concentrated in vacuo
  4. dissolutionThe residue was dissolved in 2.0 mL of H2O
  5. filtrationThe solid was filtered
  6. customdried

Sources & evidence

ORD record
ord-ee0b24e5e8104c4ca9e4428d700960b2
Source dataset
uspto-grants-2001_01
Patent number
US06177440B1

Reaction notes

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