Lithium Hydroxide → HCID 59273145, compound

HRID 1675530Notes

Reaction equation

[C:1]([C:4]1[CH:5]=[C:6]([C:13]2[CH:35]=[CH:34][C:16]([CH2:17][NH:18][C@@H:19]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:20]([O:22]C3CCCC3)=[O:21])=[CH:15][CH:14]=2)[S:7][C:8]=1[NH:9][C:10](=[O:12])[NH2:11])(=[O:3])[NH2:2].[Li+].[OH-]>O1CCCC1>[C:1]([C:4]1[CH:5]=[C:6]([C:13]2[CH:35]=[CH:34][C:16]([CH2:17][NH:18][C@@H:19]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:20]([OH:22])=[O:21])=[CH:15][CH:14]=2)[S:7][C:8]=1[NH:9][C:10](=[O:12])[NH2:11])(=[O:3])[NH2:2]

Participants

Conditions

Temperature: 40 °C

Procedure

To a solution of cyclopentyl (2S)-({-4-[4-carbamoyl-5-(carbamoylamino)-2-thienyl]benzyl}amino)(phenyl)acetate (Example 1) (50 mg, 102 μmol) in tetrahydrofuran (1 ml) was added 1.0M aq LiOH (0.508 ml, 508 μmol). The reaction was stirred at an oil bath temperature of 40° C. After 4 hours LCMS indicated 90% completion. The heating was removed and the reaction left to stir at room temperature overnight. The solvent was removed in vacuo and to the residue was added water (2 ml). 5 drops of acetic acid was added to the solution and a solid precipitated. The solid was collected by filtration and washed sequentially with water, ethanol and diethyl ether before drying under reduced pressure (26 mg, 60%).

Workup

customThe heating was removed
waitthe reaction left
stirringto stir at room temperature overnight
customThe solvent was removed in vacuo and to the residue
additionwas added water (2 ml)
addition5 drops of acetic acid was added to the solution
customa solid precipitated
filtrationThe solid was collected by filtration
washwashed sequentially with water, ethanol and diethyl ether
custombefore drying under reduced pressure (26 mg, 60%)

Sources & evidence

ORD record: ord-eb8e33bc255a437fbcc377a9976dccca
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08003695B2

Reaction notes

Loading…