Water → (r)-3-((s)-2-(4,4-Dimethyl-3-(4-(3-(2-methylphenyl)ureido)-3-hydroxybenzyl)-2,5-dioxoimidazolidin-1-yl)-2-(cyclopropylmethyl)acetylamino)-3-methylpropionic acid

HRID 1840617Notes

Reaction equation

B(Br)(Br)Br.[CH3:5][C:6]1([CH3:47])[C:10](=[O:11])[N:9]([C@@H:12]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:13]([NH:15][C@H:16]([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:8](=[O:26])[N:7]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:44])=[O:36])=[C:30]([O:45]C)[CH:29]=1.O>ClCCl>[CH3:47][C:6]1([CH3:5])[C:10](=[O:11])[N:9]([C@@H:12]([CH2:22][CH:23]2[CH2:25][CH2:24]2)[C:13]([NH:15][C@H:16]([CH3:21])[CH2:17][C:18]([OH:20])=[O:19])=[O:14])[C:8](=[O:26])[N:7]1[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][C:35]([NH:37][C:38]2[CH:43]=[CH:42][CH:41]=[CH:40][C:39]=2[CH3:44])=[O:36])=[C:30]([OH:45])[CH:29]=1

Participants

Conditions

Temperature: 0 °C

Procedure

211 μL of boron tribromide were added under argon to a solution of 100 mg (0.169 mmol) of the compound of Example 1 in 20 mL of absolute dichloromethane at −78° C. and the reaction mixture was allowed to warm to 0° C. with ice cooling. After 30 minutes at 0° C., water was cautiously added. The phases were separated and the organic phase was dried over sodium sulfate. After filtration, removal of the solvent in vacuo, chromatographic purification by preparative HPLC and freeze drying of the product fractions, 35 mg (36%) of the title compound were obtained.

Workup

customThe phases were separated
dry with materialthe organic phase was dried over sodium sulfate
filtrationAfter filtration, removal of the solvent
customin vacuo, chromatographic purification by preparative HPLC
customfreeze drying of the product fractions

Sources & evidence

ORD record: ord-8b39a3518e634d4690251a19d79510a3
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680333B2

Reaction notes

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