Phosgene → HCID 86619837, compound

HRID 1994297Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[CH2:12][NH:13][CH2:14][CH2:15][NH:16][C@H:17]([CH:25]([CH3:27])[CH3:26])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:33](Cl)(Cl)=[O:34]>C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:28]=[CH:29][CH:30]=1)[CH2:12][N:13]1[CH2:14][CH2:15][N:16]([C@H:17]([CH:25]([CH3:26])[CH3:27])[C:18]([O:20][C:21]([CH3:24])([CH3:22])[CH3:23])=[O:19])[C:33]1=[O:34])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

t-Butyl (R)-2-(2-(3-benzyloxybenzylamino)ethylamino)-3-methylbutyrate (155 mg; 0.37 mmol) was dissolved in toluene (5 ml) and cooled to 0° C. NaOH (1N; 5 ml; 5 mmol) was added, as was phosgene (20% in toluene; 0.37 ml; 0.75 mmol). The mixture was stirred at 0° C. for 6 h, the phases were separated, and the aqueous phase was extracted with CH2Cl2 (2×; 5 ml). The combined organic phases were dried over MgSO4, and the solvents were removed under reduced pressure. Purification of the residue by column chromatography (SiO2) resulted in t-butyl (R)-2-(3-(3-benzyloxybenzyl)-2-oxoimidazolidin-1-yl)-3-methylbutyrate (102 mg; 0.23 mmol). MS: 439.25 (M+H); Rt: 2.12 min (method: gradient 0 min 96% H2O (0.05% TFA) 2.0 min 95% acetonitrile, 95% acetonitrile to 2.4 min, 4% acetonitrile 2.45 min; flow rate 1 ml/min; column 0.4 μL (YMC J'sphere ODS H80 20X2 1.4μ); 30° C.)

Workup

customthe phases were separated
extractionthe aqueous phase was extracted with CH2Cl2 (2×; 5 ml)
dry with materialThe combined organic phases were dried over MgSO4
customthe solvents were removed under reduced pressure
customPurification of the residue by column chromatography (SiO2)

Sources & evidence

ORD record: ord-2fb77069a80b4d1e8b1490da6168ec36
Source dataset: uspto-grants-2010_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07652143B2

Reaction notes

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