Water → HCID 86649035, compound

HRID 1367599Notes

Reaction equation

[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16](Br)=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[O:24][CH3:25])=[O:4].[N-:26]=[N+:27]=[N-:28].[Na+].O>CC(N(C)C)=O>[CH3:1][O:2][C:3]([C@H:5]1[CH2:9][C@H:8]([S:10]([C:13]2[CH:18]=[CH:17][C:16]([N:26]=[N+:27]=[N-:28])=[CH:15][C:14]=2[C:20]([F:23])([F:22])[F:21])(=[O:12])=[O:11])[CH2:7][C@@H:6]1[O:24][CH3:25])=[O:4]

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of (1R,2R,4R) and (1S,2S,4S)-4-(4-bromo-2-trifluoromethyl-benzenesulfonyl)-2-methoxy-cyclopentanecarboxylic acid methyl ester (500 mg, 1.123 mmol, intermediate in the synthesis of example 58) in DMA (5 ml) was added sodium azide (146 mg, 2.246 mmol) and the reaction mixture was heated to 50° C. for 26 h. Then water was added and the mixture was extracted 3 times with EtOAc. The combined organic layers were dried (Na2SO4) and evaporated. The remaining brown oil was purified by silica gel chromatography (DCM/EtOAc 95:5) to obtain the title compound (351 mg, 77%) as light brown oil. MS (EI): 466.2 (M+OAc)−.

Workup

extractionthe mixture was extracted 3 times with EtOAc
dry with materialThe combined organic layers were dried (Na2SO4)
customevaporated
customThe remaining brown oil was purified by silica gel chromatography (DCM/EtOAc 95:5)

Sources & evidence

ORD record: ord-3631059c699c47a48c699971945c088a
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07893099B2

Reaction notes

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