Phosgene → HCID 24993728, compound

HRID 1673237Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([NH:10][NH2:11])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[C:16]2[O:18][C:19]([CH3:30])([CH3:29])[CH2:20][CH:21]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:26])[CH3:25])[C:15]2=[CH:14][C:13]=1[C:31]1[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=1.[C:38](Cl)(Cl)=[O:39]>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[O:9][C:38](=[O:39])[NH:11][N:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]1[N:17]=[C:16]2[O:18][C:19]([CH3:29])([CH3:30])[CH2:20][CH:21]([NH:22][C:23](=[O:28])[C:24]([CH3:27])([CH3:25])[CH3:26])[C:15]2=[CH:14][C:13]=1[C:31]1[CH:32]=[CH:33][C:34]([Cl:37])=[CH:35][CH:36]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of the product of Step C (22 mmol) in 10 mL of CH2Cl2 at −78° C. was added 300 μL of phosgene (20% in toluene). After stirring at −78° C. for 15 min and at 0° C. for 30 min, the reaction mixture was concentrated. Chromatography on a Biotage 40+S cartridge using 1:1 v/v EtOAc/hexanes as the eluant afforded the title compound: 1H NMR δ 1.27 (s, 9H), 1.48 (s, 3H), 1.56 (s, 3H), 1.86 (t, J=12.2, 1H), 2.27 (m, 1H), 5.50 (m, 1H), 5.87 (m, 1H), 6.99 (d, J=8.0, 2H), 7.17 (d, J=8.0, 2H), 7.39 (m, 1H), 7.58-7.72 (m, 3H), 9.87 (br. s, 1H).

Workup

concentrationthe reaction mixture was concentrated

Sources & evidence

ORD record: ord-801d4443a73446c68fedfda4bb9018be
Source dataset: uspto-grants-2011_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07999107B2

Reaction notes

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