Cesium carbonate → HCID 68679427, compound

HRID 2353965Notes

Reaction equation

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

Participants

Conditions

Temperature: 55 °C

Procedure

Add methyl 4-bromobutyrate (54.4 mL, 0.437 mol) to a mixture of 2-tert-butoxycarbonylamino-4-chloro-benzoic acid methyl ester (96.15 g, 0.337 mol) and Cs2CO3 (274.10 g, 0.841 mol) in DMF (1.3 L). Heat the suspension at 55° C. overnight. Remove DMF under vacuum. Dilute the organics with ethyl acetate (1.5 L) and water (1.5 L). Separate the organic layer and extract the aqueous with ethyl acetate (2×0.5 L). Combine the organics and wash with half saturated potassium bicarbonate (1 L), water (2×0.5 L) and brine (0.5 L). Dry the organics over sodium sulfate, filter, and remove solvent under vacuum. This provides the title compound as a yellow oil crude (141.8 g):

Workup

customSeparate the organic layer
extractionextract the aqueous with ethyl acetate (2×0.5 L)
washCombine the organics and wash with half saturated potassium bicarbonate (1 L), water (2×0.5 L) and brine (0.5 L)
dry with materialDry the organics over sodium sulfate
filtrationfilter
customremove solvent under vacuum

Sources & evidence

ORD record: ord-42e8de748fdc48b9ae9f08f683aa5d7f
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07749992B2

Reaction notes

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