Formaldehyde → HCID 86603940, compound

HRID 1244246Notes

Reaction equation

HRID 1244246 reaction equation
CN(C)[C:3]1[C:4]([NH:14][S:15]([C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:21][CH:22]=2)(=[O:17])=[O:16])=[CH:5][C:6]2[CH2:12][CH2:11][NH:10][CH2:9][CH2:8][C:7]=2[CH:13]=1.[CH2:31]([N:33](CC)[CH2:34]C)C.C=O.[C:40](O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:31][N:33]([C:8]1([CH3:40])[C:7]2[CH:13]=[CH:3][C:4]([NH:14][S:15]([C:18]3[S:19][C:20]([C:23]4[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)(=[O:16])=[O:17])=[CH:5][C:6]=2[CH2:12][CH2:11][NH:10][CH2:9]1)[CH3:34]

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 58613357HCID 58613357, compound

Product 1

HCID 86603940HCID 86603940, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a suspension of the intermediate D10, in 1,2-dichloroethane (1 ml) at room temperature was added triethylamine (0.3, excess) followed by 37% aqueous formaldehyde (0.2, excess). After vigorous stirring for 5 minutes, sodium triacetoxyborohydride (100 mg, excess) was added portionwise over 5 minutes and the resultant solution stirred for a further 2 hours. The reaction was partitioned between water and dichloromethane and the organic phase washed with water, brine and dried over anhydrous MgSO4. The solution was evaporated to dryness affording the title compound E16 as a pale yellow solid (20 mg, 99% ). M-H 477. 1H NMR: δ CDCl3 2.36 (3H, s), 2.44 (6H, s), 2.54 (4H, m), 2.84 (2H, m), 2.91 (2H, m), 6.87 (1H, s), 7.12 (1H, d), 7.33–7.51 (6H, m).

Workup

  1. customThe reaction was partitioned between water and dichloromethane
  2. washthe organic phase washed with water, brine
  3. dry with materialdried over anhydrous MgSO4
  4. customThe solution was evaporated to dryness

Sources & evidence

ORD record
ord-db8739dc78f64917a9333fd8cdba04f5
Source dataset
uspto-grants-2006_10
Patent number
US07122538B2

Reaction notes

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