Hydrochloric Acid → HCID 10137047, compound

HRID 895938Notes

Reaction equation

HRID 895938 reaction equation
C[O:2][C:3](=[O:32])[CH2:4][O:5][C:6]1[CH:14]=[C:13]2[CH:15]=[CH:16][CH:17]=[CH: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][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.[OH-].[Li+].Cl>O1CCCC1.O>[NH2:30][C:28](=[O:29])[C:27]([C:8]1[C:7]2[C:11](=[C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]3=[CH:14][C:6]=2[O:5][CH2:4][C:3]([OH:32])=[O:2])[N:10]([CH2:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[C:9]=1[CH3:26])=[O:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 10274713HCID 10274713, compound

Product 1

HCID 10137047HCID 10137047, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-[[3-(2-amino-1,2-dioxoethyl)-1-cyclohexylmethyl-2-methyl-1H-benz[g]indol-4-yl]oxy]acetic acid methyl ester (0.042 g, 0.096 mmol) in 60% tetrahydrofuran/40% methanol (5 mL) was added 1 M lithium hydroxide solution (3 mL). The resulting mixture was stirred at room temperature for 28 h. The mixture was warmed briefly, diluted with water, and acidified with concentrated hydrochloric acid. The resulting yellow precipitate was collected via vacuum filtration and air-dried to provide 0.022 g (54%) of the title compound. 1H NMR (DMSO-d6) δ13.00 (bs, 1H), 8.22 (d, J=8.4 Hz, 1H), 7.85 (d, J=7.3 Hz, 1H), 7.73 (bs, 1H), 7.48 (t, J=7.0 Hz, 1H), 7.45 (bs, 1H), 7.39 (t, J=7.0 Hz, 1H), 6.91 (s, 1H), 4.76 (s, 2H), 4.45 (bs, 2H), 2.55 (s, 3H), 1.90 (bs, 1H), 1.60 (m, 5H), 1.10 (m, 5H).

Workup

  1. temperatureThe mixture was warmed briefly
  2. filtrationThe resulting yellow precipitate was collected via vacuum filtration
  3. customair-dried

Sources & evidence

ORD record
ord-6a68f411fa0445e2823973ccc6ffa807
Source dataset
uspto-grants-2005_07
Patent number
US06916840B2

Reaction notes

Loading…