Bromoacetonitrile → HCID 58630868, compound

HRID 1823332Notes

Reaction equation

HRID 1823332 reaction equation
Cl.Cl.[NH2:3][C@@H:4]([C@H:20]([O:22][CH3:23])[CH3:21])[CH2:5][S:6]([CH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:8])=[O:7].Br[CH2:25][C:26]#[N:27].C(N(C(C)C)C(C)C)C>C(#N)C>[C:26]([CH2:25][NH:3][C@@H:4]([C@H:20]([O:22][CH3:23])[CH3:21])[CH2:5][S:6]([CH2:9][C:10]1[CH:11]=[N:12][C:13]2[C:18]([CH:19]=1)=[CH:17][CH:16]=[CH:15][CH:14]=2)(=[O:7])=[O:8])#[N:27]

Participants

5

Reactant 3

HCID 11534BromoacetonitrileHCID 81531DiisopropylethylamineHCID 69656099HCID 69656099, compound

Product 1

HCID 58630868HCID 58630868, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of (2S,3R)-2-amino-3-methoxy-1-(3-quinolylmethanesulfonyl)butane dihydrochloride (0.93 g), bromoacetonitrile (0.41 ml) and N-ethyldiisopropylamine (1.7 ml) in acetonitrile (15 ml) was refluxed for 16 h, cooled and evaporated. The residue was partitioned between MDC (15 ml) and saturated sodium hydrogen carbonate solution (15 ml). The organic phase was collected and the aqueous re-extracted with MDC (15 ml). The combined MDC phases were dried (MgSO4) and evaporated. The residue was flash chromatographed (silica gel, step gradient: 70–100% EtOAc/hexane) to give the subtitle compound (0.59 g). MS (APCI+ve ion) 348(MH+); 1H NMR δ(CDCl3): 8.91 (1H, m), 8.3 (1H, d, J=2 Hz), 8.14 (1H, d, J=8 Hz), 7.78 (1H, d, J=8 Hz), 7.78 (1H, t, J=8 Hz), 7.60 (1H, t, J=8 Hz), 4.55 (2H, s), 3.4–3.88 (4H, m), 3.33 (3H, s), 2.93–3.28 (2H, m), 2.18 (1H, m), 0.93 (3H, d, J=6.3 Hz).

Workup

  1. temperaturewas refluxed for 16 h
  2. temperaturecooled
  3. customevaporated
  4. customThe residue was partitioned between MDC (15 ml) and saturated sodium hydrogen carbonate solution (15 ml)
  5. customThe organic phase was collected
  6. extractionthe aqueous re-extracted with MDC (15 ml)
  7. dry with materialThe combined MDC phases were dried (MgSO4)
  8. customevaporated
  9. customchromatographed (silica gel, step gradient: 70–100% EtOAc/hexane)

Sources & evidence

ORD record
ord-4e6174f20bb445d2b9aa9537a3d0ad4e
Source dataset
uspto-grants-2006_05
Patent number
US07038055B2

Reaction notes

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