Lithium Hydroxide → HCID 10159102, compound

HRID 489115Notes

Reaction equation

HRID 489115 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH2:15][CH2:16][CH2:17][CH2:18][C:12]2=[C:11]2[C:7]=1[C:8]([C:27](=[O:31])[C:28]([NH2:30])=[O:29])=[C:9]([CH3:26])[N:10]2[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Li+]>CO.O>[NH2:30][C:28](=[O:29])[C:27]([C:8]1[C:7]2[C:11](=[C:12]3[CH2:18][CH2:17][CH2:16][CH2:15][C:13]3=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:32])=[O:2])[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]=1[CH3:26])=[O:31]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 10160055HCID 10160055, compound

Product 1

HCID 10159102HCID 10159102, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-1-benzyl-2-methyl-6,7,8,9-tetrahydro-1H-benz[g]indol-4-yl]oxy]acetic acid methyl ester (285 mg, 0.671 mmol) in methanol (5 ml) was treated with 1 M lithium hydroxide solution (2.5 mL) at room temperature for 1.5 h. The reaction mixture was diluted with water, concentrated in vacuo, and treated with 1 M hydrochloric acid (1 mL). The resulting precipitate was collected via vacuum filtration and dried to provide 270 mg (96%) of the title compound as a tan powder: mp>300° C. 1H NMR (DMSO-d6) δ 8.00 (bs, 1H), 7.35 (m, 3H), 7.26 (t, J=7.0 Hz, 1H), 6.88 (d, J=7.3 Hz, 2H), 6.21 (s, 1H), 5.64 (s, 2H), 4.38 (s, 2H), 2.88 (m, 2H), 2.71 (m, 2H), 2.35 (s, 3H), 1.60 (m, 4H); MS ES+ m/e 421 (p+1); IR (KBr, cm−1) 1636, 1402.

Workup

  1. concentrationconcentrated in vacuo
  2. additiontreated with 1 M hydrochloric acid (1 mL)
  3. filtrationThe resulting precipitate was collected via vacuum filtration
  4. customdried

Sources & evidence

ORD record
ord-a13f0e09a5174074b96c55f1bc41c14d
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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