Potassium Carbonate → methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoate

HRID 1674546Notes

Reaction equation

HRID 1674546 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][NH:15][S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][CH2:37][CH:38]=[CH2:39]>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:14][N:15]([CH2:39][CH2:38][CH2:37][CH:36]=[CH2:35])[S:16]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[N+:25]([O-:27])=[O:26])(=[O:18])=[O:17])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 707041-Pentene, 5-bromo-HCID 58798583methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitrophenylsulfonamido)propanoate

Product 1

HCID 58798683methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoateYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitrophenylsulfonamido)propanoate iii (150 mg, 0.37 mmol) in 3 mL of DMF was added potassium carbonate (102 mg, 0.74 mmol.). This mixture was stirred at rt for 20 min followed by the addition of 5-bromo-1-pentene (65 □L, 0.55 mmol.). The reaction mixture was stirred at rt for 2 days. It was then filtered, concentrated and purified by silica gel chromatography (eluting with 25% ethyl acetate in hexane) to give 75 mg (43%) of methyl 2(S)-(tert-butoxycarbonylamino)-3-(2-nitro-N-(pent-4-enyl)phenylsulfonamido)propanoate iv as a yellow solid. 1H NMR (CD3OD, 300 MHz) δ 1.42 (s, 9H), 1.54-1.64 (m, 2H), 1.97 (q, J=7.20 Hz, 2H), 3.37 (m, 2H), 3.57-3.80 (m, 2H), 3.72 (s, 3H), 4.42 (dd, J=8.60, 5.31 Hz, 1H), 4.91-5.01 (m, 2H), 5.69-5.79 (m, 1H), 7.75-7.85 (m, 3H), 8.04 (m, 1H); MS m/z 372 (M++1-Boc).

Workup

  1. stirringThe reaction mixture was stirred at rt for 2 days
  2. filtrationIt was then filtered
  3. concentrationconcentrated
  4. custompurified by silica gel chromatography (eluting with 25% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f8e41e4ae2f344a9be08ead19a6df1ea
Source dataset
uspto-grants-2011_08
Patent number
US08003604B2

Reaction notes

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