Lithium Hydroxide → HCID 15454797, compound
Reaction equation
[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:14]2[N:15]=[C:16]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[C:23]([O:25]CC)=[O:24])[S:17][CH:18]=2)[S:12][CH:13]=1)=[O:8].[Li+].[OH-]>>[CH3:1][S:2][CH2:3][CH2:4][CH2:5][NH:6][C:7]([C:9]1[N:10]=[C:11]([C:14]2[N:15]=[C:16]([CH2:19][CH2:20][NH:21][C:22](=[O:28])[C:23]([OH:25])=[O:24])[S:17][CH:18]=2)[S:12][CH:13]=1)=[O:8]Participants
Conditions
- Temperature
- 25 °C
Procedure
A solution of 118 (12.7 mg, 0.029 mmol) in THF-H2O--CH3OH (3:1:1, 0.45 mL) was treated with LiOH (6.0 mg, 0.14 mmol, 5.0 equiv) and the mixture was stirred at 25° C. for 2 h before the solvent was removed in vacuo. The crude product was dissolved in H2O and was acidified to pH 0.5 with the addition of 10% aqueous HCl. The product was extracted with 30% isopropanol-CHCl3 (7×1.2 mL), and the combined extracts were concentrated to afford 119 (11.9 mg, 11.9 mg theoretical, 100%) as an off white solid which was sufficiently pure to use in the next reaction directly: 1H NMR (CD3OD, 400 MHz) 8.16 (s, 1H), 8.14 (s, 1H), 3.71 (t, J=6.8 Hz, 2H), 3.51 (t, J=7.0 Hz, 2H), 3.30 (t, 2H, overlapped with CH3OH), 2.58 (t, J=7.2 Hz, 2H), 2.10 (s, 3H), 1.92 (tt, J=7.2, 7.0 Hz, 2H); IR (film)max 3346, 3102, 2916, 1656, 1543, 1480, 1436, 1362, 1294, 1240, 1128, 1054 cm-1 ; FABHRMS (NBA) m/z (M++H, C15H18N4O4S3 requires 415.0568).
Workup
- customwas removed in vacuo
- dissolutionThe crude product was dissolved in H2O
- additionwas acidified to pH 0.5 with the addition of 10% aqueous HCl
- extractionThe product was extracted with 30% isopropanol-CHCl3 (7×1.2 mL)
- concentrationthe combined extracts were concentrated
Sources & evidence
- ORD record
- ord-f3f351d39c4e4d09967c51b63323b81b
- Source dataset
- uspto-grants-2000_05
- Patent number
- US06060608
Reaction notes
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