Dimethylformamide dimethyl acetal → HCID 21905771, compound

HRID 2054402Notes

Reaction equation

HRID 2054402 reaction equation
[CH3:1]OC(OC)N(C)C.[CH:9]([N:22]1[CH2:25][C:24]([NH:29][CH3:30])([C:26]([NH2:28])=[O:27])[CH2:23]1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>>[CH:9]([N:22]1[CH2:25][C:24]2([C:26](=[O:27])[N:28]=[CH:30][N:29]2[CH3:1])[CH2:23]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 58721711HCID 58721711, compound

Product 1

HCID 21905771HCID 21905771, compoundYield 96%

Procedure

N,N-Dimethylformamide dimethyl acetal (1.1 ml, 8.3 mmol) was combined with 1-benzhydryl-3-methylaminoazetidine-3-carboxylic acid amide (I-3A-2b; 153 mg, 0.52 mmol) and heated to reflux. After 3 hours, the suspension was cooled and extracted from saturated aqueous NaHCO3 with ethyl acetate. The combined extracts were dried (Na2SO4), and concentrated, in vacuo, to afford I-3A-4a as a solid (152 mg, 96%): +ESI MS (M+1) 306.3; 1H NMR (400 MHz, CD3OD) δ 8.42 (s, 1H), 7.47 (d, J=7.5 Hz, 4H), 7.27 (t, J=7.5 Hz, 4H), 7.17 (t, J=7.5 Hz, 2H), 4.57 (s, 1H), 3.58 (s, 3H), 3.55 (d, J=10.0 Hz, 2H), 3.34 (d, J=10.0 Hz, 2H).

Workup

  1. temperatureheated to reflux
  2. temperaturethe suspension was cooled
  3. extractionextracted from saturated aqueous NaHCO3 with ethyl acetate
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. concentrationconcentrated, in vacuo

Sources & evidence

ORD record
ord-7a85ac168ec24d76bb476312c915299a
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

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