Dimethylformamide dimethyl acetal → HCID 21905833, compound

HRID 2054404Notes

Reaction equation

HRID 2054404 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-2A-1d; 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 the 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-5a 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, to the crude solid (3.50 g)
  6. customPurification of the residue on a Biotage™ Flash 40M column

Sources & evidence

ORD record
ord-c6b9061140d64bd9b28334ce5ea6d199
Source dataset
uspto-grants-2008_02
Patent number
US07329658B2

Reaction notes

Loading…