N-bromobutanimide → HCID 11694443, compound

HRID 2237448Notes

Reaction equation

HRID 2237448 reaction equation
C(OC([N:6]1[CH2:12][CH2:11][C:10]2[CH:13]=[CH:14][S:15][C:9]=2[CH:8]([CH3:16])[CH2:7]1)=O)C.C1C(=O)N([Br:24])C(=O)C1>C(Cl)(Cl)Cl.CC(O)=O>[Br:24][C:14]1[S:15][C:9]2[CH:8]([CH3:16])[CH2:7][NH:6][CH2:12][CH2:11][C:10]=2[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59302555HCID 59302555, compound

Product 1

HCID 11694443HCID 11694443, compound

Reagents, catalysts & solvents 1

HCID 21584526Acetic acid chloroformSolvent

Conditions

Temperature
100 °C

Procedure

The product of step f) was dissolved in 2 mL of 1:1 CHCl3/HOAc and treated with NBS (62 mg, 0.35 mmol). After stirring for 10 minutes, the reaction was concentrated to dryness and filtered through a pad of silica gel, eluting with EtOAc. The eluent was concentrated and the residue was treated with 2 mL each EtOH and 40% aqueous KOH. After heating for 14 hours at 100° C., the reaction was diluted with water and extracted 2× into DCM. The title compound was purified by preparative HPLC-MS. The two enantiomers were separated using a Chiralpak® AD-RH® 20×250 mm column from Chiral Technologies (10 mL/min MeOH mobile phase) to give enantiomer 1 (rt=11.6 minutes) and enantiomer 2 (rt=13.6 minutes) of the title compound. 1H NMR (CD3OD) δ 6.92 (s, 1H), 3.48-3.34 (m, 3H), 3.17-2.99 (m, 4H), 1.44 (d, J=7.2 Hz, 3H); MS: ESI (positive): 246, 248 (M+H).

Workup

  1. concentrationthe reaction was concentrated to dryness
  2. filtrationfiltered through a pad of silica gel
  3. washeluting with EtOAc
  4. concentrationThe eluent was concentrated
  5. additionthe residue was treated with 2 mL each EtOH and 40% aqueous KOH
  6. additionthe reaction was diluted with water
  7. extractionextracted 2× into DCM
  8. customThe title compound was purified by preparative HPLC-MS
  9. customThe two enantiomers were separated

Sources & evidence

ORD record
ord-ba40019928c3499da2ea8f2d542467e4
Source dataset
uspto-grants-2010_05
Patent number
US07718647B2

Reaction notes

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