Lithium Hydroxide → HCID 68866473, compound

HRID 1725911Notes

Reaction equation

F[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:22]([O:24]C)=[O:23])(=[O:10])=[O:9].C(N(CC)CC)C.[CH2:33]([NH2:37])[CH2:34][CH2:35][CH3:36].[Li+].[OH-]>C(#N)C>[CH2:33]([NH:37][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH:11][C:12]1[CH:21]=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]=1[C:22]([OH:24])=[O:23])(=[O:10])=[O:9])[CH2:34][CH2:35][CH3:36]

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of Example 133B (0.060 g, 0.17 mmol), triethylamine (0.070 mL, 0.50 mmol), and butylamine (0.088 mL, 0.85 mmol) in anhydrous acetonitrile (0.6 mL) was heated to 200° C. for 20 minutes in a microwave reactor and concentrated. The concentrate was dissolved in 9:1 methanol/water (1 mL), treated with LiOH (25 mg, 0.6 mmol), and heated to 65° C. for 16 hours. The reaction mixture was concentrated and the concentrate was purified by C18 reverse-phase HPLC using acetonitrile/water/0.1% TFA to provide the desired product. MS (DCI) m/e 399 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ 13.73 (br s, 1H), 10.30 (br s, 1H), 8.16 (br s, 1H), 7.88 (m, 2H), 7.57 (m, 2H), 7.49 (t, 1H), 7.34 (m, 1H), 7.26 (d, 1H), 6.72 (d, 1H), 6.59 (t, 1H), 5.87 (br s, 1H), 3.04 (t, 2H), 1.41 (quint, 2H), 1.26 (sext, 2H), 0.82 (t, 3H).

Workup

concentrationconcentrated
dissolutionThe concentrate was dissolved in 9:1 methanol/water (1 mL)
concentrationThe reaction mixture was concentrated
customthe concentrate was purified by C18 reverse-phase

Sources & evidence

ORD record: ord-e75bb631da594dd0a767992841e654c6
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491718B2

Reaction notes

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