Water → 4-[4-(3-nitro-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 388281Notes

Reaction equation

HRID 388281 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([S:10](Cl)(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:36]3[O:35][CH2:34][CH2:33][NH:32][C:31]=3[CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15].N1C=CC=CC=1.O>ClCCl>[C:14]([O:18][C:19]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[C:36]3[O:35][CH2:34][CH2:33][N:32]([S:10]([C:6]4[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=4)(=[O:12])=[O:11])[C:31]=3[CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 84763-Nitrobenzenesulfonyl chlorideHCID 207656864-(3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 207656854-[4-(3-nitro-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl]-piperazine-1-carboxylic acid tert-butyl esterYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-Nitro-benzenesulfonyl chloride (122.9 mg, 0.55 mmol) was added in small portions under nitrogen to an ice-cold solution of 4-(3,4-dihydro-2H-benzo[1,4]oxazin-8-yl)-piperazine-1-carboxylic acid tert-butyl ester (161 mg, 0.504 mmol) and pyridine (88 mg, 1.11 mmol) in dichlormethane (2 mL). After 0.5 hour at ambient temperature, water was added. The organic phase was separated, washed with saturated aqueous solution of sodium bicarbonate (20 mL), dried (Na2SO4) and concentrated to give 4-[4-(3-nitro-benzenesulfonyl)-3,4-dihydro-2H-benzo[1,4]oxazin-8-yl]-piperazine-1-carboxylic acid tert-butyl ester as an oil (260 mg). MS: MH+=505.

Workup

  1. customThe organic phase was separated
  2. washwashed with saturated aqueous solution of sodium bicarbonate (20 mL)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-5dae263d2a79402c91336ec8dd7d636d
Source dataset
uspto-grants-2013_02
Patent number
US08377931B2

Reaction notes

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