Triphosgene → HCID 71090272, compound

HRID 716828Notes

Reaction equation

[NH2:1][C@H:2]([CH2:24][CH3:25])[C:3]([NH:5][C:6]1[CH:7]=[N:8][C:9]([O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[CH2:18][O:17][C:16]3([CH3:23])[CH3:22])=[CH:10][CH:11]=1)=[O:4].[C:26](=O)(OC(Cl)(Cl)Cl)[O:27]C(Cl)(Cl)Cl>C(Cl)Cl>[CH3:23][C:16]1([CH3:22])[C:15]2[C:19](=[CH:20][CH:21]=[C:13]([O:12][C:9]3[N:8]=[CH:7][C:6]([N:5]4[C:3](=[O:4])[C@@H:2]([CH2:24][CH3:25])[NH:1][C:26]4=[O:27])=[CH:11][CH:10]=3)[CH:14]=2)[CH2:18][O:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of (2R)-2-amino-N-[6-[(3,3-dimethyl-1H-isobenzofuran-5-yl)oxy]-3-pyridyl]butanamide (Intermediate 61, 18 mg, 0.0527 mmol) in DCM (4 mL) N,N-diethylethanamine (0.022 ml, 0.16 mmol) was added and the reaction mixture was cooled to 0° C. A solution of bis(trichloromethyl) carbonate (7.8 mg, 0.026 mmol) in DCM (1 mL) was slowly added and the reaction mixture was stirred for 30 minutes at the same temperature. The reaction was diluted with DCM (5 ml) and washed with an aqueous saturated solution of NH4Cl (10 ml). The organic layer was dried (Na2SO4), filtered and evaporated and the residue was purified by flash chromatography (Biotage system) on silica gel using a SNAP 10 g as column and cyclohexane/ethyl acetate from 80:20 to 10:90 as eluent affording the title compound (16 mg) as white solid.

Workup

washwashed with an aqueous saturated solution of NH4Cl (10 ml)
dry with materialThe organic layer was dried (Na2SO4)
filtrationfiltered
customevaporated
customthe residue was purified by flash chromatography (Biotage system) on silica gel using a SNAP 10 g as column and cyclohexane/ethyl acetate from 80:20 to 10:90 as eluent

Sources & evidence

ORD record: ord-d17d9aa9aad24873851d4f1e3b76ea39
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193704B2

Reaction notes

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