Ethyl Acetate → HCID 58043132, compound

HRID 1035224Notes

Reaction equation

[SH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][CH:3]=1.CS(O[CH:17]1[CH2:20][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:18]1)(=O)=O.C([O-])([O-])=O.[Cs+].[Cs+].CCOC(C)=O>CN(C=O)C>[CH3:9][O:8][C:6]([C:5]1[CH:4]=[CH:3][C:2]([S:1][CH:17]2[CH2:18][N:19]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:20]2)=[CH:11][CH:10]=1)=[O:7]

Participants

Conditions

Temperature: 90 °C

Procedure

Methyl 4-mercaptobenzoate (3.00 g, 17.8 mmol) and tert-butyl 3-(methylsulfonyloxy)azetidine-1-carboxylate (4.48 g, 17.8 mmol) were dissolved in DMF (30 mL). Cs2CO3 (6.97 g, 21.4 mmol) was added and the mixture was stirred at 90° C. for 3 hours, then cooled to room temperature. EtOAc (50 ml) was added and the solids were filtered off. The filtrate was washed with a saturated aqueous K2CO3 solution (20 mL), dried (MgSO4) and then evaporated. The residue was purified by column chromatography eluting with heptane, EtOAc/heptane (5:95, then 10:90). There was obtained 3.10 g (53%) of 59A as a solid. 1H NMR (500 MHz, CDCl3): δ 1.45 (s, 9H), 3.89 (m, 2H), 3.90 (s, 3H), 4.11 (m, 1H), 4.42 (t, 2H), 7.16 (d, 2H), 7.95 (d, 2H).

Workup

temperaturecooled to room temperature
filtrationthe solids were filtered off
washThe filtrate was washed with a saturated aqueous K2CO3 solution (20 mL)
dry with materialdried (MgSO4)
customevaporated
customThe residue was purified by column chromatography
washeluting with heptane, EtOAc/heptane (5:95

Sources & evidence

ORD record: ord-1a3f4f925d93480d8fd2947ef42ffe36
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546375B2

Reaction notes

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