Water → HCID 70790589, compound

HRID 1971742Notes

Reaction equation

HRID 1971742 reaction equation
[C:1]([N:5]1[CH2:37][CH2:36][C:35](C)(C)[CH2:34][C:8]2[CH:9]=[C:10]3[C:19]4[CH:18]=[C:17]([C@@H:20]5[O:24][C:23]([CH3:26])([CH3:25])[O:22][C@H:21]5[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:16]([O:32][CH3:33])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:40])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:48])C(=O)C1.O>CN(C=O)C>[C:1]([N:5]1[CH2:37][CH2:36][CH2:35][CH2:34][C:8]2[C:9]([Br:48])=[C:10]3[C:19]4[CH:18]=[C:17]([C@@H:20]5[O:24][C:23]([CH3:26])([CH3:25])[O:22][C@H:21]5[C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:16]([O:32][CH3:33])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:40])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 86650573HCID 86650573, compound

Product 1

HCID 70790589HCID 70790589, compoundYield 104.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 0.95 g of 21d in 10 ml of DMF was treated with 0.32 g of NBS. The reaction was stirred for 1 hr and then poured into water and extracted with ethyl acetate. The extract was washed with water, dried and concentrated and the product filtered through silica gel (using a gradient of heptane-ethylacetate as eluent), to provide 1.08 gr of 21e; LC-MS-ESI: [M+1] 603.13, 605.13. NMR (CDCl3) δ 8.57 and 6.70 (2×s, 2, Ar—H), 5.51 (d, 1, CHO), 4.20 (m, 2, CHO and ethyl ester), 1.25 (t, 3, ethyl ester), 4.32+3.80 (2×m, 2, CH2), 3.78 (3, 3, OCH3), 3.75 (and 3.50 (2×m, 2, CH2), 2.95 and 3.05 (2×m, 2, CH2), 2.65 and 2.70 (2×m, 2, CH2) 1.65-2.0 (bm, 4, 2×CH2) 1.62 and 1.64 (2×s, 6, dimethylketal) 1.57 (s, 9, tertC4H9)

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water
  3. customdried
  4. concentrationconcentrated
  5. filtrationthe product filtered through silica gel (

Sources & evidence

ORD record
ord-9219140427904f74840dd4bd10f2f5e5
Source dataset
uspto-grants-2013_04
Patent number
US08431564B2

Reaction notes

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