Benzaldehyde → HCID 10024568, compound

HRID 460011Notes

Reaction equation

HRID 460011 reaction equation
[C:1]([C:3]1[C:4]([CH3:29])=[C:5]([N:16]2[CH2:21][CH2:20][N:19]([C:22](OC(C)(C)C)=O)[CH2:18][CH2:17]2)[S:6][C:7]=1[NH:8][C:9](=[O:15])[CH:10]([CH2:13][CH3:14])[CH2:11][CH3:12])#[N:2].FC(F)(F)C(O)=O.C(=O)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.ClC(Cl)C>[CH2:22]([N:19]1[CH2:18][CH2:17][N:16]([C:5]2[S:6][C:7]([NH:8][C:9](=[O:15])[CH:10]([CH2:11][CH3:12])[CH2:13][CH3:14])=[C:3]([C:1]#[N:2])[C:4]=2[CH3:29])[CH2:21][CH2:20]1)[C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1

Participants

7

Reactant 4

HCID 240BenzaldehydeHCID 6422Trifluoroacetic acidHCID 5049666Sodium triacetoxyborohydrideHCID 10432291HCID 10432291, compound

Product 1

HCID 10024568HCID 10024568, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a solution of 1.06 g (2.52 mmol) of the title compound from Example 30 in 10 mL of CH2Cl2 was added 10 mL of trifluoroacetic acid. After 2 h at ambient temperature the reaction was concentrated in vacuo. To 0.040 g (0.092 mmol) of this intermediate in 1 mL of dichloroethane was added 0.032 mL (0.20 mmol) of benzaldehyde, followed by 0.066 g (0.31 mmol) of sodium triacetoxyborohydride. After 16 h at ambient temperature the reaction was quenched by the addition of 10 mL of saturated aqueous NaHCO3. The reaction was extracted with CH2Cl2 and the organic layer was dried (Na2SO4) and concentrated in vacuo. Purification by preparative thin layer chromatography (15% EtOAc in hexane) afforded the title compound as a white solid. 1H NMR (500 MHz, CDCl3) 8.69 (s, 1H), 7.35 (m, 5H), 3.72 (s, 1H), 3.57 (s, 1H), 2.94 (t, J=5.0 Hz, 4H), 2.58 (s, 4H), 2.26 (m, 1H), 2.16 (s, 3H), 1.73 (m, 2H), 1.61 (m, 2H), 0.95 (t, J=7.5 Hz, 6H); mass spectrum (ES) m/e=411.2 (M+H).

Workup

  1. concentrationAfter 2 h at ambient temperature the reaction was concentrated in vacuo
  2. customAfter 16 h at ambient temperature the reaction was quenched by the addition of 10 mL of saturated aqueous NaHCO3
  3. extractionThe reaction was extracted with CH2Cl2
  4. dry with materialthe organic layer was dried (Na2SO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by preparative thin layer chromatography (15% EtOAc in hexane)

Sources & evidence

ORD record
ord-8c5e70b197df4c4fa7be7ca2f5e941d0
Source dataset
uspto-grants-2007_03
Patent number
US07196106B2

Reaction notes

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