Sodium Azide → HCID 42633023, compound

HRID 1674682Notes

Reaction equation

HRID 1674682 reaction equation
[N-:1]=[N+]=[N-].[Na+].C(OC([N:12]1[CH2:17][C@@H:16]([CH2:18]OS(C2C=CC(C)=CC=2)(=O)=O)[C@H:15]([C:30]2[CH:35]=[CH:34][C:33]([CH2:36][O:37][CH2:38][C@H:39]([O:41][CH2:42][CH3:43])[CH3:40])=[CH:32][CH:31]=2)[C@@H:14]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][C:49]3[O:54][CH2:53][CH2:52][N:51]([CH2:55][CH2:56][CH2:57][O:58][CH3:59])[C:50]=3[CH:60]=2)[CH2:13]1)=O)(C)(C)C>CN1CCCN(C)C1=O.CC(OC)(C)C>[CH2:42]([O:41][C@H:39]([CH3:40])[CH2:38][O:37][CH2:36][C:33]1[CH:34]=[CH:35][C:30]([C@@H:15]2[C@@H:14]([O:44][CH2:45][C:46]3[CH:47]=[CH:48][C:49]4[O:54][CH2:53][CH2:52][N:51]([CH2:55][CH2:56][CH2:57][O:58][CH3:59])[C:50]=4[CH:60]=3)[CH2:13][NH:12][CH2:17][C@H:16]2[CH2:18][NH2:1])=[CH:31][CH:32]=1)[CH3:43]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86648138HCID 86648138, compound

Product 1

HCID 42633023HCID 42633023, compound

Reagents, catalysts & solvents 2

HCID 15413tert-Butyl methyl etherSolventHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent

Procedure

4.57 mmol of sodium azide are added to a solution of 0.91 mmol of (3R,4R,5S)-4-[4-((R)-2-ethoxy-propoxymethyl)-phenyl]-3-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-5-(toluene-4-sulfonyloxymethyl)-piperidine-1-carboxylic acid tert-butyl ester (example 5d) in 5 ml of 1,3-dimethyl-tetrahydro-pyrimidin-2-one (DMPU) under argon at 50° C. After 2 h, the reaction mixture is cooled to RT, diluted with TBME, washed successively with H2O (2×) and brine, dried over Na2SO4 and concentrated by evaporation. The title compound is obtained from the residue by means of flash chromatography (SiO2 60F) as a pale yellow oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.27 (EtOAc/heptane 1:1); Rt=5.98 (gradient I).

Workup

  1. washwashed successively with H2O (2×) and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-fbf648ba11d048ea9174bb8472421724
Source dataset
uspto-grants-2011_08
Patent number
US08003640B2

Reaction notes

Loading…