Potassium Carbonate → HCID 21080148, compound

HRID 346962Notes

Reaction equation

HRID 346962 reaction equation
[C:1]([O:5][C:6]([C@@H:8]([CH2:13][NH:14][S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:34][CH2:35][CH2:36][CH:37]=[CH2:38]>CN(C=O)C>[C:1]([O:5][C:6]([C@@H:8]([CH2:13][N:14]([CH2:38][CH2:37][CH2:36][CH:35]=[CH2:34])[S:15]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[N+:24]([O-:26])=[O:25])(=[O:17])=[O:16])[C:9]([O:11][CH3:12])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 707041-Pentene, 5-bromo-HCID 68747691HCID 68747691, compound

Product 1

HCID 21080148HCID 21080148, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (S)-methyl 2-(tert-butoxycarbonyl)-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 μL, 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 (S)-methyl 2-(tert-butoxycarbonyl)-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). LC-MS (Method D, retention time: 2.68 min), 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-6ab85be91d434f5bab691669a9e02109
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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