Heptane → HCID 53240891, compound

HRID 1475961Notes

Reaction equation

HRID 1475961 reaction equation
[C:1]([O:4][NH:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7])(=[O:3])[CH3:2].[H-].[Na+].[Br:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[S:22](Cl)(=[O:24])=[O:23].CCCCCCC>C1COCC1.C(OCC)(=O)C>[C:1]([O:4][N:5]([S:22]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[Br:15])(=[O:24])=[O:23])[C:6](=[O:7])[O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:3])[CH3:2]

Participants

7

Reactant 4

HCID 8900HeptaneHCID 24758Sodium hydrideHCID 5204032-Bromobenzenesulfonyl chlorideHCID 10058028(Acetyloxy)-carbamic acid tert-butyl ester

Product 1

HCID 53240891HCID 53240891, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl (acetyloxy)[(2-bromophenyl)sulfonyl]carbamate (41) is prepared according to Scheme 2. A solution of [(tert-butoxy)carbonyl]amino acetate (0.68 g, 3.9 mmol) in THF (5 ml) is added dropwise to a stirred solution of sodium hydride (0.16 g of a 60% dispersion, 3.9 mmol) in THF (10 ml). Stirring is continued for 30 minutes, whereupon 2-bromobenzene sulfonyl chloride (1.0 g, 3.9 mmol) is added. The reaction mixture is stirred at room temperature for 3 hours after which time tlc (1:1 heptane:ethyl acetate) shows no starting material remains. The reaction mixture is quenched by the addition of water (30 ml) and extracted into ether (2×50 ml). The combined organics are dried over sodium sulfate, filtered and concentrated in vacuo to yield the desired material as a yellow oil, which is purified by silica column chromatography eluting with heptane: ethyl acetate (4:1; v:v). (0.96 g, 60%), 1H NMR (360 MHz, DMSO-d6) δ ppm 8.12-8.26 (1H, m), 7.87-8.06 (1H, m), 7.61-7.79 (2H, m), 2.32 (3H, s), 1.26 (9H, s).

Workup

  1. additionis added
  2. customThe reaction mixture is quenched by the addition of water (30 ml)
  3. extractionextracted into ether (2×50 ml)
  4. dry with materialThe combined organics are dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f5f218fcabf648d58d868e5b93b7b7a4
Source dataset
uspto-grants-2015_04
Patent number
US09018411B2

Reaction notes

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