p-Toluenesulfonic acid → HCID 57518686, compound

HRID 1258125Notes

Reaction equation

HRID 1258125 reaction equation
[CH3:1][C@:2]1([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[CH2:6][CH2:5][C@@H:4]([CH2:7][C:8]2N=C(C(F)(F)F)[O:10][N:9]=2)[C:3]1([CH3:18])[CH3:17].CC1C=CC(S(O)(=O)=O)=CC=1.[C:38](#[N:42])[CH:39]([CH3:41])[CH3:40]>[Cl-].[Cl-].[Zn+2]>[CH:39]([C:38]1[O:10][N:9]=[C:8]([CH2:7][C@@H:4]2[CH2:5][CH2:6][C@@:2]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:1])[C:3]2([CH3:18])[CH3:17])[N:42]=1)([CH3:41])[CH3:40]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 6559Isobutyronitrile2×HCID 57518676HCID 57518676, compound

Product 1

HCID 57518686HCID 57518686, compound

Reagents, catalysts & solvents 1

HCID 3007855ZincchlorideCatalyst

Conditions

Temperature
92.5 °C

Procedure

To a solution of tert-butyl {(1S,3S)-3-[(2Z)-2-amino-2-(hydroxyimino)ethyl]-1,2,2-trimethylcyclopentyl}carbamate (prepared in Step-1 example 56) (0.300 g, 1.0 mmoles) in isobutyronitrile (7 mL), ZnCl2 (0.0410 g, 3.0 mmol), PTSA (0.057 g, 3.0 mmol) were added under N2 atmosphere. It was heated to 90-95° C. for six hours. After completion of reaction, isopropyl cyanide was removed under reduced pressure and diluted with water and ethyl acetate. The layers are separated and the organic layer was dried over Na2SO4, and concentrated on a rotavapor. The crude material is purified by column. 0.120 g, Off white sticky mass, 1H NMR (400 MHz, CDCl3) δ ppm: 0.81 (s, 3H), 0.97 (s, 3H), 1.21 (s, 3H), 1.34 (d, 6H), 1.43 (s, 9H), 1.70-1.73 (m, 1H), 1.95-2.00 (m, 2H), 2.22-2.25 (m, 2H), 2.55-2.59 (m, 1H), 2.79-2.83 (m, 1H), 3.17-3.19 (m, 1H), 4.51 (s, 1H). m/z (M−100)+H, 252.2.

Workup

  1. customwas removed under reduced pressure
  2. additiondiluted with water and ethyl acetate
  3. customThe layers are separated
  4. dry with materialthe organic layer was dried over Na2SO4
  5. concentrationconcentrated on a rotavapor
  6. customThe crude material is purified by column

Sources & evidence

ORD record
ord-6f5978bf156f4daa8a10b01883947dc3
Source dataset
uspto-grants-2013_06
Patent number
US08466145B2

Reaction notes

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