Phosgene → (S)-[3-(1-cyclopropylmethyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-yl)-2-oxo-oxazolidin-5-ylmethyl]-carbamic acid tert-butyl ester

HRID 2114904Notes

Reaction equation

[C:1](Cl)(Cl)=[O:2].[C:5]([O:9][C:10](=[O:32])[NH:11][CH2:12][C@H:13]([OH:31])[CH2:14][NH:15][C:16]1[CH:17]=[C:18]2[C:22](=[C:23]([F:25])[CH:24]=1)[N:21]([CH2:26][CH:27]1[CH2:29][CH2:28]1)[C:20](=[O:30])[CH2:19]2)([CH3:8])([CH3:7])[CH3:6].C(N(CC)CC)C>ClCCl>[C:5]([O:9][C:10](=[O:32])[NH:11][CH2:12][C@@H:13]1[O:31][C:1](=[O:2])[N:15]([C:16]2[CH:17]=[C:18]3[C:22](=[C:23]([F:25])[CH:24]=2)[N:21]([CH2:26][CH:27]2[CH2:28][CH2:29]2)[C:20](=[O:30])[CH2:19]3)[CH2:14]1)([CH3:8])([CH3:6])[CH3:7]

Participants

Conditions

Temperature: 0 °C

Procedure

Phosgene (20% solution in toluene, 1.50 ml, 14.1 mmol) is added to (R)-[3-(1-cyclopropylmethyl-7-fluoro-2-oxo-2,3-dihydro-1H-indol-5-ylamino)-2-hydroxy-propyl]-carbamic acid tert-butyl ester (0.74 g, 1.88 mmol) and triethylamine (0.95 ml, 9.41 mmol) in dichloromethane (15 ml) at 0° C. and then stirred at 0° C. for 20 minutes. The mixture is diluted with dichloromethane, washed with water and brine, dried (Na2SO4) and evaporated. The residue is purified by flash column chromatography (70% ethyl acetate/hexane) to give the title compound as a white solid. HPLC r.t. 5.39 min; MS for C21H26FN3O5 m/z 420.1 (M+H)+.

Workup

washwashed with water and brine
dry with materialdried (Na2SO4)
customevaporated
customThe residue is purified by flash column chromatography (70% ethyl acetate/hexane)

Sources & evidence

ORD record: ord-b43036e2e3054149bee39c769ec575d5
Source dataset: uspto-grants-2008_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07435751B2

Reaction notes

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