Tin tetrachloride → HCID 86673682, compound

HRID 2273060Notes

Reaction equation

HRID 2273060 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][NH:6]2.Cl[Sn](Cl)(Cl)Cl.C(O[C@H:31]1[C@H:35]([O:36][C:37](=[O:39])[CH3:38])[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][C@@H:45]([N:67]=[N+:68]=[N-:69])[CH2:46][CH2:47][C@H:48]([NH:56][S:57]([C:60]2[CH:65]=[CH:64][C:63]([CH3:66])=[CH:62][CH:61]=2)(=[O:59])=[O:58])[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[O:32]1)(=O)C>ClC(Cl)C>[C:37]([O:36][C@@H:35]1[C@H:34]([O:40][C:41](=[O:43])[CH3:42])[C@@H:33]([CH2:44][C@@H:45]([N:67]=[N+:68]=[N-:69])[CH2:46][CH2:47][C@H:48]([NH:56][S:57]([C:60]2[CH:65]=[CH:64][C:63]([CH3:66])=[CH:62][CH:61]=2)(=[O:58])=[O:59])[C:49]([O:51][C:52]([CH3:55])([CH3:54])[CH3:53])=[O:50])[O:32][C@H:31]1[N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][C:9]([NH:11][CH2:12][CH2:13][NH:14][C:15]([O:16][C:17]([CH3:18])([CH3:20])[CH3:19])=[O:21])=[N:10][C:2]=2[NH2:1])(=[O:39])[CH3:38]

Participants

5

Reactant 3

HCID 24287Tin tetrachlorideHCID 14563628HCID 14563628, compoundHCID 178453680HCID 178453680, compound

Product 1

HCID 86673682HCID 86673682, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a mixture consisting of Compound 27A (10 molar equivalents) in an appropriate solvent is added SnCl4 (equimolar) in dichloroethane. A mixture consisting of (2S,3R,4R,5R)-5-((2S,5S)-2-azido-6-(tert-butoxy)-5-(4-methylphenylsulfonamido)-6-oxohexyl)tetrahydrofuran-2,3,4-triyl triacetate (limiting reagent, prepared in the manner of Rapoport et. al. as 25β) is added and the mixture stirred at room temperature for 16 hours. The mixture is partitioned between ethyl acetate and 0.5N Na2HPO4 and the organics washed with brine, dried and evaporated. The residue is chromatographed on silica gel to obtain the title intermediate.

Workup

  1. customprepared in the manner of Rapoport et. al. as 25β)
  2. additionis added
  3. customThe mixture is partitioned between ethyl acetate and 0.5N Na2HPO4
  4. washthe organics washed with brine
  5. customdried
  6. customevaporated
  7. customThe residue is chromatographed on silica gel

Sources & evidence

ORD record
ord-089a0b64f0064d27a7f716d37b3395c6
Source dataset
uspto-grants-2015_09
Patent number
US09120820B2

Reaction notes

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