Sodium Azide → HCID 44184304, compound

HRID 910483Notes

Reaction equation

HRID 910483 reaction equation
[CH2:1]([O:3][C@H:4]([CH3:54])[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)CN(S(C3C=CC(C)=CC=3)(=O)=O)[C@@H](CCOS(C)(=O)=O)[CH2:15]2)=[CH:10][CH:9]=1)[CH3:2].[N-]=[N+:56]=[N-:57].[Na+].[CH3:59][N:60]1[C:65](=O)[N:64]([CH3:67])[CH2:63][CH2:62][CH2:61]1>CC(OC)(C)C>[CH2:1]([O:3][C@H:4]([CH3:54])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@H:14]2[CH2:15][C@H:63]([CH2:62][CH2:61][N:60]3[CH:65]=[N:57][N:56]=[CH:59]3)[NH:64][CH2:67][C@@H:19]2[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)=[CH:10][CH:9]=1)[CH3:2]

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 86649419HCID 86649419, compound

Product 1

HCID 44184304HCID 44184304, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent

Procedure

A solution of 1.0 mmol of methanesulfonic acid 2-[(2R,4R,5R)-4-[4-((R)-2-ethoxy-propoxymethyl) -phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-ethyl ester (example 6g) and 10 mmol of sodium azide in 1.5 ml of DMPU is stirred at 80° C. for 3 h. The solution is cooled to RT, diluted with 3 ml of TBME, filtered through 2 cm of SiO2 60 F, eluting with EtOAc-Heptane 1:1. The filtrate is concentrated under reduced pressure and purified by flash chromatography (SiO2 60 F), to afford the title compound as a yellow oil. Rf=0.45 (EtOAc/heptane 2:1); Rt=5.80 (gradient I).

Workup

  1. filtrationfiltered through 2 cm of SiO2 60 F
  2. washeluting with EtOAc-Heptane 1:1
  3. concentrationThe filtrate is concentrated under reduced pressure
  4. custompurified by flash chromatography (SiO2 60 F)

Sources & evidence

ORD record
ord-ea464a8a6c4944d7a1e9ad725d2e70ac
Source dataset
uspto-grants-2011_09
Patent number
US08022069B2

Reaction notes

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