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

HRID 2358350Notes

Reaction equation

HRID 2358350 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 98.3%

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, 9 H), 3.36-3.51 (m, 2 H), 3.71 (s, 3 H), 4.22 (m, 1 H), 7.80-7.90 (m, 3 H), 8.07-8.10 (m, 1 H).

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-4d9a69958e9a4b9f8b7bb8b30a2aae1d
Source dataset
uspto-grants-2010_07
Patent number
US07763584B2

Reaction notes

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