2-Nitrobenzenesulfonyl chloride → methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitrophenylsulfonamido)propanoate

HRID 1674545Notes

Reaction equation

HRID 1674545 reaction equation
[NH2:1][CH2:2][C@H:3]([NH:8][C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[C:4]([O:6][CH3:7])=[O:5].CCN(C(C)C)C(C)C.[N+:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35])([O-:27])=[O:26]>C(Cl)Cl>[C:12]([O:11][C:9]([NH:8][C@@H:3]([CH2:2][NH:1][S:34]([C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=1[N+:25]([O-:27])=[O:26])(=[O:35])=[O:36])[C:4]([O:6][CH3:7])=[O:5])=[O:10])([CH3:15])([CH3:14])[CH3:13]

Participants

5

Reactant 3

HCID 155402-Nitrobenzenesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 11746086(S)-Methyl 3-amino-2-((tert-butoxycarbonyl)amino)propanoate

Product 1

HCID 58798583methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitrophenylsulfonamido)propanoateYield 98.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 3-amino-2(S)-(tert-butoxycarbonylamino)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 methyl 2(S)-(tert-butoxycarbonylamino)-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-4e31f78f246c40f1b3872760ed0e8c25
Source dataset
uspto-grants-2011_08
Patent number
US08003604B2

Reaction notes

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