Water → (4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine

HRID 276289Notes

Reaction equation

HRID 276289 reaction equation
Cl.[C:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@@H:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:13][S:12]2)=[C:6]([CH2:24][CH3:25])[CH:5]=1)#[N:3].O.C([O-])(O)=O.[Na+]>CCOC(C)=O>[C:2]([C:4]1[CH:9]=[CH:8][C:7]([N:10]=[C:11]2[N:15]([CH2:16][CH:17]([CH3:19])[CH3:18])[C@@H:14]([CH2:20][CH:21]([CH3:23])[CH3:22])[CH2:13][S:12]2)=[C:6]([CH2:24][CH3:25])[CH:5]=1)#[N:3]

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 69993363(4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine HCl salt

Product 1

HCID 57065163(4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of (4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine HCl salt (Method C6a; 304 g, 0.8 mol), water (1 L) and EtOAc (1.4 L) was added NaHCO3 (150 g, 1.78 mol, 2.2 equiv.). The resulting mixture was stirred for 1 h. The organic layer was dried (MgSO4) and concentrated under reduced pressure. The resulting viscous oil was treated with EtOH and concentrated under reduced pressure twice to afford (4S)-2-(4-cyano-2-ethylphenylimino)-3,4-diisobutyl-1,3-thiazolidine as a low melting solid (264 g, 96%): mp 50° C.; [a]D=+2.4, (c 1.0, CH3OH); 1H NMR (CDCl3) 0.92-0.99 (m, 12H), 1.13 (t, J=7.4 Hz, 3H), 1.47-1.52 (m, 1H), 1.58-1.67 (m, 2H), 2.07-2.11 (m, 1H), 2.54 (q, J=7.4 Hz, 2H), 2.84-2.90 (m, 2H), 3.28 (dd, J=10.6, 6.6 Hz, 1H), 3.68 (dd, J=13.6, 8.1, Hz, 1H), 3.81-3.87 (m, 1H), 6.85 (d, J=7.9 Hz, 1H), 7.36-7.42 (m, 2H); CI-MS m/z 344 ((M+H)+).

Workup

  1. dry with materialThe organic layer was dried (MgSO4)
  2. concentrationconcentrated under reduced pressure
  3. additionThe resulting viscous oil was treated with EtOH
  4. concentrationconcentrated under reduced pressure twice

Sources & evidence

ORD record
ord-3cae616730ff44cba2e98853173b6b9c
Source dataset
uspto-grants-2002_03
Patent number
US06353006B1

Reaction notes

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