Lithium Hydroxide → HCID 10113775, compound

HRID 489114Notes

Reaction equation

HRID 489114 reaction equation
C[O:2][C:3](=[O:33])[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:28](=[O:32])[C:29]([NH2:31])=[O:30])=[C:9]([CH2:26][CH3:27])[N:10]2[CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[OH-].[Li+]>O1CCCC1.CO>[NH2:31][C:29](=[O:30])[C:28]([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:33])=[O:2])[N:10]([CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:9]=1[CH2:26][CH3:27])=[O:32]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 10114687HCID 10114687, compound

Product 1

HCID 10113775HCID 10113775, compoundYield 88.2%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-1-benzyl-2-ethyl-6,7,8,9-tetrahydro-1H-benz[g]indol-4-yl]oxy]acetic acid methyl ester (150 mg, 0.334 mmol) in 3:1 tetrahydrofuran/methanol (4 mL) was treated with 1 M lithium hydroxide solution (1 mL) at room temperature for 1 h. The reaction mixture was concentrated in vacuo to one half the original volume and treated with 1 M hydrochloric acid (1 mL). The resulting suspension was diluted with water (5 mL), stirred, and the precipitate collected via vacuum filtration. This material was washed with water and dried to provide 128 mg (88%) of the title compound as a yellow solid: mp 222-225° C. 1H NMR (DMSO-d6) δ 7.72 (bs, 1H), 7.33 (m, 0.4H), 6.87 (d, J=7.3 Hz, 2H), 6.23 (s, 1H), 5.65 (s, 2H), 4.56 (s, 2H), 2.87 (m, 2H), 2.72 (m, 4H), 1.59 (m, 4H), 1.07 (t, J=7.3 Hz, 3H); MS ES+ m/e 435 (p+1); IR (CHCl3, cm−1) 3507, 3472, 3393, 2938, 1759, 1640.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to one half the original volume
  2. additiontreated with 1 M hydrochloric acid (1 mL)
  3. additionThe resulting suspension was diluted with water (5 mL)
  4. filtrationthe precipitate collected via vacuum filtration
  5. washThis material was washed with water
  6. customdried

Sources & evidence

ORD record
ord-523bced00ea94edba40956c60c3b5e09
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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