Hydrochloric Acid → HCID 10163133, compound

HRID 489117Notes

Reaction equation

HRID 489117 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][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[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[Br:25].[OH-].[Li+].Cl>CO.O>[NH2:30][C:28](=[O:29])[C:27]([C:8]1[C:7]2[C:11](=[C:12]3[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]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Br:25])[C:9]=1[CH3:26])=[O:31]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 101177372-[[3-(2-Amino-1,2-dioxoethyl)-2-methyl-1-(2-bromobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester

Product 1

HCID 10163133HCID 10163133, compoundYield 35.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of 2-[[3-(2-amino-1,2-dioxoethyl)-2-methyl-1-(2-bromobenzyl)-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (106 mg, 0.21 mmol) in methanol (3 mL) was treated with 1 N lithium hydroxide solution (1 mL). The solution was heated to reflux then allowed to cool to room temperature. The mixture was diluted with water and acidified with 1 N hydrochloric acid. The resulting precipitate was collected via vacuum filtration and washed carefully with ethyl acetate to provide 36 mg (35%) of the title compound as a tan solid: mp 261-262° C. (dec). 1H NMR (DMSO-d6) δ 12.88 (bs, 1H), 7.72 (m, 2H), 7.43 (bs, 1H), 7.26 (m, 2H), 6.46 (s, 1H), 6.18 (m, 1H), 5.48 (s, 2H), 4.62 (s, 2H), 2.80 (m, 4H), 2.43 (s, 3H), 1.93 (quintet, J=7.3 Hz, 2H); IR (KBr, cm−1) 3431, 1735, 1628, 1213.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux
  3. filtrationThe resulting precipitate was collected via vacuum filtration
  4. washwashed carefully with ethyl acetate

Sources & evidence

ORD record
ord-f018c77c6f76401798c85e010697ade4
Source dataset
uspto-grants-2005_12
Patent number
US06974831B2

Reaction notes

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