Lithium Hydroxide → HCID 10273637, compound

HRID 489101Notes

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]([CH2:25][CH3:26])[N:10]2[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.[OH-].[Li+]>O1CCCC1.CO>[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][CH:20]=2)[C:9]=1[CH2:25][CH3:26])=[O:31]

Participants

Conditions

Temperature: 40 °C

Procedure

A solution 2-[[3-(2-amino-1,2-dioxoethyl)-2-ethyl-1-benzyl-1,6,7,8-tetrahydrocyclopent[g]indol-4-yl]oxy]acetic acid methyl ester (10 mg, 0.023 mmol) in 1:1 tetrahydrofuran/methanol (3 mL) was treated with 1 M aqueous lithium hydroxide solution (1.5 mL) The resulting mixture was warmed to 40° C. and stirred for 2 h. The mixture was concentrated in vacuo and treated with dilute hydrochloric acid. The resulting precipitate was collected via vacuum filtration. The solid was slurried with methanol, and the resulting solid collected via vacuum filtration to provide 5 mg (52%) of the title product as a white solid. 1H NMR (CDCl3) δ 7.25 (m, 3H), 7.03 (bs, 1H, —NH), 6.90 (d, J=6 Hz, 2H), 6.57 (s, 1H), 6.45 (bs, 1H, —NH), 5.50 (s, 2H), 4.77 (s, 2H), 2.90 (m, 6H), 2.04 (quintet, J=7 Hz, 2H), 1.18 (t, J=7 Hz, 3H); TOS MS ES+ exact mass calculated for C24H25N2O5 (p+1): m/z=421.1763. Found: 421.1767.

Workup

concentrationThe mixture was concentrated in vacuo
additiontreated with dilute hydrochloric acid
filtrationThe resulting precipitate was collected via vacuum filtration
filtrationthe resulting solid collected via vacuum filtration

Sources & evidence

ORD record: ord-d9b03632d14442958a12882b221aa60c
Source dataset: uspto-grants-2005_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06974831B2

Reaction notes

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