Potassium tert-butoxide → HCID 42626244, compound

HRID 1174320Notes

Reaction equation

[CH3:1]C(C)([O-])C.[K+].[C:7]([C:10]1[N:15]=[C:14]([CH2:16][N:17]2[CH2:21][CH2:20][N:19]([C@@H:22]([C:30]([CH3:33])([CH3:32])[CH3:31])[C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:18]2=[O:34])[CH:13]=[CH:12][CH:11]=1)(=O)[CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1>[C:7]([C:10]1[N:15]=[C:14]([CH2:16][N:17]2[CH2:21][CH2:20][N:19]([C@@H:22]([C:30]([CH3:33])([CH3:31])[CH3:32])[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[C:18]2=[O:34])[CH:13]=[CH:12][CH:11]=1)([CH3:1])=[CH2:8]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of methyltriphenylphosphonium bromide (0.33 g, 0.923 mmol) in THF (2.5 mL) was treated with a solution of potassium tert-butoxide in THF (0.89 mL, 1 M) dropwise, stirred for 1 hour at 25° C., treated with a solution of the product from Example 117A (0.116 g, 0.298 mmol) in THF (2 mL), stirred at 25° C. for 16 hours, quenched with saturated ammonium chloride solution and partitioned between ethyl acetate and water. The organic phase was washed with brine and dried over MgSO4, filtered and concentrated. The residue was chromatographed on silica gel eluting with 15%-25% ethyl acetate in hexane to give the title compound (0.040 g, 35% yield).

Workup

stirringstirred at 25° C. for 16 hours
customquenched with saturated ammonium chloride solution
custompartitioned between ethyl acetate and water
washThe organic phase was washed with brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was chromatographed on silica gel eluting with 15%-25% ethyl acetate in hexane

Sources & evidence

ORD record: ord-639488a421b842e9ac1beaa8b4e97780
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07834043B2

Reaction notes

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