Ammonium Chloride → HCID 90301194, compound

HRID 627652Notes

Reaction equation

HRID 627652 reaction equation
[C:1]([O:5][C:6]([N:8]([C:16]1[C:21]([CH3:23])([CH3:22])[S:20](=[O:25])(=[O:24])[CH2:19][C@:18]([C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=2[F:36])([CH3:26])[N:17]=1)[C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].C[Si]([N-][Si](C)(C)C)(C)C.C1C=CC(S(N(S(C2C=CC=CC=2)(=O)=O)[F:57])(=O)=O)=CC=1.[Cl-].[NH4+]>C1COCC1>[C:11]([O:10][C:9]([N:8]([C:16]1[C:21]([CH3:23])([CH3:22])[S:20](=[O:25])(=[O:24])[CH:19]([F:57])[C@:18]([C:27]2[CH:32]=[C:31]([N+:33]([O-:35])=[O:34])[CH:30]=[CH:29][C:28]=2[F:36])([CH3:26])[N:17]=1)[C:6](=[O:7])[O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:15])([CH3:12])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 588007N-FluorobenzenesulfonimideHCID 2733832Lithium HexamethyldisilazideHCID 86728128HCID 86728128, compound

Product 1

HCID 90301194HCID 90301194, compoundYield 52.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyl N-tert-butoxycarbonyl-N-[(3R)-3-(2-fluoro-5-nitro-phenyl)-3,6,6-trimethyl-1,1-dioxo-2H-1,4-thiazin-5-yl]carbamate (bis-boc intermediate) (2.03 g, 3.83 mmol)) in THF (24 mL) was cooled to −78° C. LHMDS (1.0 M in THF; 4.02 ml, 4.02 mmol) was added dropwise and the reaction was stirred at −78° C. for 1 hour. To this was added N-fluorobenzenesulfonimide (1.813 g, 5.75 mmol) as a solution in THF (4 mL). The reaction was stirred at −78° C. for 30 minutes. The reaction was treated with aqueous ammonium chloride solution and extracted with ethyl acetate. The organic portion was e dried over Na2SO4, filtered, concentrated and purified by column chromatography, eluting with 0-40% tert-butyl methyl ether in Heptanes to afford the title compound (1.1 g, 2.01 mmol, 52.4% yield) as a mixture of diastereomers. MS m/z=570.0 (M+Na).

Workup

  1. stirringThe reaction was stirred at −78° C. for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by column chromatography
  7. washeluting with 0-40% tert-butyl methyl ether in Heptanes

Sources & evidence

ORD record
ord-bcb64b41076745a6b888f8bd16192789
Source dataset
uspto-grants-2016_04
Patent number
US09309263B2

Reaction notes

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