Dimethylformamide dimethyl acetal → HCID 21905833, compound

HRID 915849Notes

Reaction equation

HRID 915849 reaction equation
[CH3:1]OC(OC)N(C)C.[CH:9]([N:22]1[CH2:25][C:24]([NH:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)([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[CH2:23][C:24]2([C:26](=[O:27])[N:28]=[CH:1][N:29]2[CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:25]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 587217091-(Diphenylmethyl)-3-[(phenylmethyl)amino]-3-azetidinecarboxamide

Product 1

HCID 21905833HCID 21905833, compoundYield 62%

Procedure

N,N-Dimethylformamide dimethyl acetal (16 ml, 121 mmol) was combined with 1-benzhydryl-3-benzylaminoazetidine-3-carboxylic acid amide (I-3A-50b; 3.03 g, 8.16 mmol) and heated to reflux. After 4 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 give a crude solid (3.50 g). Purification of the residue on a Biotage™ Flash 40M column using 0-3% methanol in methylene chloride as eluant afforded I-3A-50c as a yellowish solid (1.92 g, 62%): +ESI MS (M+1) 382.3; 1H NMR (400 MHz, CD3OD) δ 8.66 (s, 1H), 7.59 (d, J=7.1 Hz, 2H), 7.49-7.11 (m, 13H), 5.12 (s, 2H), 4.44 (s, 1H), 3.31 (d, J=9.6 Hz, 2H), 3.20 (d, J=9.6 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
  6. customto give a crude solid (3.50 g)
  7. customPurification of the residue on a Biotage™ Flash 40M column

Sources & evidence

ORD record
ord-a56a8e3542b040a5a1793bc3cba4e2e4
Source dataset
uspto-grants-2007_09
Patent number
US07268133B2

Reaction notes

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