Dimethylformamide dimethyl acetal → HCID 87254173, compound

HRID 910811Notes

Reaction equation

HRID 910811 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:52])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[C@@H:16]([CH2:47][C:48]([NH:50][NH2:51])=[O:49])[CH2:15]2)=[CH:10][CH:9]=1.CO[CH:55](OC)[N:56]([CH3:58])[CH3:57]>C(Cl)Cl>[CH3:55][N:56]([CH3:58])/[CH:57]=[N:51]/[NH:50][C:48](=[O:49])[CH2:47][C@H:16]1[CH2:15][C@H:14]([C:11]2[CH:10]=[CH:9][C:8]([CH2:7][O:6][CH2:5][C@@H:4]([CH3:52])[CH2:3][O:2][CH3:1])=[CH:13][CH:12]=2)[C@@H:19]([O:20][CH2:21][C:22]2[CH:23]=[CH:24][C:25]3[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=3[CH:36]=2)[CH2:18][N:17]1[S:37]([C:40]1[CH:41]=[CH:42][C:43]([CH3:46])=[CH:44][CH:45]=1)(=[O:38])=[O:39]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 67061822HCID 67061822, compound

Product 1

HCID 87254173HCID 87254173, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 1 mmol of [(2R,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-acetic acid hydrazide in 5 ml of CH2Cl2 is treated at RT with 1.1 mmol of N,N-dimethylformamide dimethylacetal and refluxed for 1 h. The mixture is cooled to RT, and concentrated under reduced pressure to afford the title compound as a viscous brown-orange oil. Rt=4.75 (gradient I).

Workup

  1. temperaturerefluxed for 1 h
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c8e15293bb9d451c842e71a7309eff3d
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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