Lithium Hydroxide → HCID 19002307, compound

HRID 2260013Notes

Reaction equation

[CH2:1]([O:3][O:4][P:5]([C:11]([F:33])([F:32])[C:12]1[CH:31]=[CH:30][C:15]([CH2:16][CH:17]([C:26]([O:28]C)=[O:27])[NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:14][CH:13]=1)([O:7][O:8][CH2:9][CH3:10])=[O:6])[CH3:2].[Li+].[OH-]>C1COCC1>[CH2:1]([O:3][O:4][P:5]([C:11]([F:33])([F:32])[C:12]1[CH:13]=[CH:14][C:15]([CH2:16][CH:17]([C:26]([OH:28])=[O:27])[NH:18][C:19]([O:21][C:22]([CH3:24])([CH3:25])[CH3:23])=[O:20])=[CH:30][CH:31]=1)([O:7][O:8][CH2:9][CH3:10])=[O:6])[CH3:2]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 42 (536 mg, 1.15 mmol) in THF (10 mL) at 0° C. was added 0.2 N LiOH (6.3 mL, 1.3 mmol, 1.1 equivalents) at 0° C. dropwise over 15 minutes. The reaction was then stirred at 0° C. and monitored by TLC with four additions of 576 μL (0.115 mmol, 0.1 equivalents) 0.2 N LiOH over a 2 hour period. The reaction mixture was then partitioned between ice-cold 0.2 N HCl/brine and EtOAc (3×75 mL); dried (MgSO4) and solvent removed by rotovap (20° C.) to yield 33 as a foam (500 mg, 96%). 1H NMR (250 MHz, CDCl3 +D2O) δ:7.46 (d, 2H, J=8.1 Hz, aromatic), 7.21 (d, 2H, J=8.1 Hz, aromatic), 4.57 (m, 1H, Hα), 4.10 (m, 4H, OCH2), 3.11 (m, 2H, Hβ), 1.36 (s, 9H, C(CH3)3), 1.23 (2 t, 6H, J=7.1 Hz, CH3); FABMS m/z 452.1 (M+H)+.

Workup

customThe reaction mixture was then partitioned between ice-cold 0.2 N HCl/brine and EtOAc (3×75 mL)
dry with materialdried (MgSO4) and solvent
customremoved by rotovap (20° C.)

Sources & evidence

ORD record: ord-2b2be450a28d4bf29f73945bc1aa82b6
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05475129

Reaction notes

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