Sodium Azide → HCID 86746815, compound

HRID 248270Notes

Reaction equation

HRID 248270 reaction equation
[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:67])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47](OS(C3C=CC=CC=3[N+]([O-])=O)(=O)=O)[CH:46](OC(C)C)[CH2:45]2)[CH:7]([CH3:68])[CH:6]([O:69][Si:70]([C:73]([CH3:76])([CH3:75])[CH3:74])([CH3:72])[CH3:71])[CH2:5][C:4]1=[O:77])[CH3:2].[N-]=[N+]=[N-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([CH:3]1[CH:29]=[C:28]([CH3:30])[CH2:27][CH:26]([CH3:31])[CH2:25][CH:24]([O:32][CH3:33])[CH:23]2[O:34][C:19]([OH:38])([CH:20]([CH3:37])[CH2:21][CH:22]2[O:35][CH3:36])[C:18](=[O:39])[C:17](=[O:40])[N:16]2[CH:11]([CH2:12][CH2:13][CH2:14][CH2:15]2)[C:10](=[O:41])[O:9][CH:8]([C:42]([CH3:67])=[CH:43][CH:44]2[CH2:49][CH2:48][CH:47]([O:9][CH:8]([CH3:42])[CH3:7])[CH2:46][CH2:45]2)[CH:7]([CH3:68])[CH:6]([O:69][Si:70]([C:73]([CH3:75])([CH3:76])[CH3:74])([CH3:72])[CH3:71])[CH2:5][C:4]1=[O:77])[CH3:2]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 57244958HCID 57244958, compound

Product 1

HCID 86746815HCID 86746815, compoundYield 106.5%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 17-ethyl-1-hydroxy-14-(tert-butyldimethylsiloxy)-12-[2'-(4"-(o-nitrophenyl-sulfonyloxy)-3"-isopropyloxycyclohexyl)-1'-methylvinyl]-23,25-dimethoxy-13,19,21,27-tetramethyl-11,28-dioxa-4-azatricyclo[22.3.1.04,9 ]octacos-18-ene-2,3,10,16-tetraone (87 mg) in N,N-dimethyl formamide (1 ml) was added an excess of sodium azide (25 mg) and the mixture heated to 70° C. After 7.5 hours the reaction was cooled to room temperature, diluted with ethyl acetate, extracted from half-saturated ammonium chloride, and washed with brine. The combined organics were dried over sodium sulfate and purified by flash chromatography on silica gel (ethyl acetate:hexane (1:2)+1% methanol) to give the title compound (38 mg).

Workup

  1. temperatureAfter 7.5 hours the reaction was cooled to room temperature
  2. extractionextracted from half-saturated ammonium chloride
  3. washwashed with brine
  4. dry with materialThe combined organics were dried over sodium sulfate
  5. custompurified by flash chromatography on silica gel (ethyl acetate:hexane (1:2)+1% methanol)

Sources & evidence

ORD record
ord-88f1ef5992b3491fb8ef6e0fcc94bb5e
Source dataset
uspto-grants-1993_05
Patent number
US05208228

Reaction notes

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