Water → HCID 131735721, compound

HRID 2201725Notes

Reaction equation

HRID 2201725 reaction equation
[CH3:1][C:2]([Si:5]([CH3:27])([CH3:26])[O:6][C@@H:7]1[CH2:20][C@@H:19]2[C@H:10]([C@H:11]3[C@H:16]([CH2:17][CH2:18]2)[CH2:15][C@:14]2([CH3:25])[C:21](=O)[CH2:22][CH2:23][C@H:13]2[CH2:12]3)[CH2:9][CH2:8]1)([CH3:4])[CH3:3].Cl.[NH2:29][OH:30].O>N1C=CC=CC=1>[CH3:1][C:2]([Si:5]([CH3:27])([CH3:26])[O:6][C@@H:7]1[CH2:20][C@@H:19]2[C@H:10]([C@H:11]3[C@H:16]([CH2:17][CH2:18]2)[CH2:15][C@:14]2([CH3:25])[C:21](=[N:29][OH:30])[CH2:22][CH2:23][C@H:13]2[CH2:12]3)[CH2:9][CH2:8]1)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 90388579HCID 90388579, compound

Product 1

HCID 131735721HCID 131735721, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 4 (130 mg, 0.33 mmol) in pyridine (10 mL) was added hydroxylamine hydrochloride (140 mg, 2.0 mmol) at room temperature. After 14 h, water was added and the product extracted into EtOAc (50 mL×2). The combined extracts were dried, filtered and removed. The residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes) to afford compound 5 (105 mg, 82%): 1H NMR (CDCl3) δ 9.00 (s, br, 1H), 3.95-4.00 (m, 1H), 2.45-2.51 (m, 2H), 0.87 (s, 9H), 0.01 (s, 6H); 13C NMR (CDCl3) δ 171.0, 66.7, 48.5, 48.1, 47.4, 44.0, 41.9, 41.4, 38.2, 36.2, 34.1, 33.7, 27.9, 25.8, 25.4, 25.0, 23.4, 18.1, 17.0, −4.96, −4.91.

Workup

  1. extractionthe product extracted into EtOAc (50 mL×2)
  2. customThe combined extracts were dried
  3. filtrationfiltered
  4. customremoved
  5. customThe residue was purified by flash column chromatography (silica gel eluted with 10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-209f5d8e6b9a407a8cc87bde03acf430
Source dataset
uspto-grants-2016_06
Patent number
US09365502B2

Reaction notes

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