Sodium Azide → HCID 86629099, compound

HRID 1863978Notes

Reaction equation

HRID 1863978 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[CH2:5]([O:12][C:13]([N:15]1[CH2:20][C@@H:19]([CH2:21]OS(C2C=CC(C)=CC=2)(=O)=O)[C@H:18]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][O:40][CH2:41][C@@H:42]([CH3:46])[CH2:43][O:44][CH3:45])=[CH:35][CH:34]=2)[C@@H:17]([O:47][CH2:48][C:49]2[CH:50]=[CH:51][C:52]3[O:57][CH2:56][CH2:55][N:54]([CH2:58][CH2:59][CH2:60][O:61][CH3:62])[C:53]=3[CH:63]=2)[CH2:16]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1>CN1CCCN(C)C1=O.COC(C)(C)C>[CH2:5]([O:12][C:13]([N:15]1[CH2:16][C@H:17]([O:47][CH2:48][C:49]2[CH:50]=[CH:51][C:52]3[O:57][CH2:56][CH2:55][N:54]([CH2:58][CH2:59][CH2:60][O:61][CH3:62])[C:53]=3[CH:63]=2)[C@@H:18]([C:33]2[CH:38]=[CH:37][C:36]([CH2:39][O:40][CH2:41][C@@H:42]([CH3:46])[CH2:43][O:44][CH3:45])=[CH:35][CH:34]=2)[C@H:19]([CH2:21][N:1]=[N+:2]=[N-:3])[CH2:20]1)=[O:14])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86629100HCID 86629100, compound

Product 1

HCID 86629099HCID 86629099, compound

Reagents, catalysts & solvents 2

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

Procedure

31.265 mmol of sodium azide are added to a solution of 6.253 mmol of (3R,4R,5S)-4-[4-((S)-3-methoxy-2-methyl-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 benzyl ester in 50 ml of 1,3-dimethyl-tetrahydro -pyrimidin-2-one (DMPU) under argon at 45° C. After 5 hours, the reaction mixture is cooled to room temperature, diluted with tert-butyl methyl ether, washed with water and brine, dried with sodium sulfate and evaporated. The crude title compound is obtained as a yellow oil. Rf=0.58 (EtOAc-heptane 2:1); Rt=5.96 (gradient I).

Workup

  1. washwashed with water and brine
  2. dry with materialdried with sodium sulfate
  3. customevaporated

Sources & evidence

ORD record
ord-99b578cbe17241e08ecefbccf44e2eb9
Source dataset
uspto-grants-2009_12
Patent number
US07625893B2

Reaction notes

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