2-Nitrobenzenesulfonyl chloride → HCID 68747691, compound

HRID 346961Notes

Reaction equation

HRID 346961 reaction equation
[NH2:1][CH2:2][C@H:3]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[N+:24]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1[S:33](Cl)(=[O:35])=[O:34])([O-:26])=[O:25]>C(Cl)Cl>[C:11]([O:10][C:8]([C@@H:3]([CH2:2][NH:1][S:33]([C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[N+:24]([O-:26])=[O:25])(=[O:34])=[O:35])[C:4]([O:6][CH3:7])=[O:5])=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 86597624HCID 86597624, compound

Product 1

HCID 68747691HCID 68747691, compoundYield 102.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of (S)-methyl 3-amino-2-(tert-butoxycarbonyl)propanoate ii (1.6 g, 7.3 mmoL) in DCM (50 mL) was added DIPEA (1.64 mL, 9.4 mmoL) and 2-nitrobenzene sulfonyl chloride (1.62 g, 7.3 mmoL). The mixture was stirred at rt for 2 h. It was then concentrated, dissolved in ethyl acetate, which was then washed with sat. sodium bicarbonate, brine and dried over magnesium sulfate. It was then filtered, concentrated to yield 2.9 g (98%) of (S)-methyl 2-(tert-butoxycarbonyl)-3-(2-nitrophenylsulfonamido)propanoate iii as a yellow foam. 1H NMR (CD3OD, 300 MHz) δ 1.41 (s, 9H), 3.36–3.51 (m, 2H), 3.71 (s, 3H), 4.22 (m, 1H), 7.80–7.90 (m, 3H), 8.07–8.10 (m, 1H).

Workup

  1. concentrationIt was then concentrated
  2. dissolutiondissolved in ethyl acetate
  3. washwhich was then washed with sat. sodium bicarbonate, brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationIt was then filtered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3eccacbfba954c18af7da28ecace91fb
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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