Diisopropylethylamine → HCID 57562539, compound

HRID 1725623Notes

Reaction equation

HRID 1725623 reaction equation
C(N(C(C)C)CC)(C)C.[C:10]([O:14][C:15]([NH:17][C@@H:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:19][SH:20])=[O:16])([CH3:13])([CH3:12])[CH3:11].[N+:25](/[CH:28]=[CH:29]/[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)([O-:27])=[O:26]>C(#N)C>[C:10]([O:14][C:15]([NH:17][C@@H:18]([C:21]([O:23][CH3:24])=[O:22])[CH2:19][S:20][CH:29]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:28][N+:25]([O-:27])=[O:26])=[O:16])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 5284459beta-nitrostyrene, (E)-HCID 10922492HCID 10922492, compound

Product 1

HCID 57562539HCID 57562539, compoundYield 91.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Diisopropylethylamine (3.38 mL, 19.4 mmol) was added to a solution of methyl N-(tert-butoxycarbonyl)-D-cysteinate (3.04 g, 12.9 mmol) and □-trans-nitrostyrene (1.93 g, 12.92 mmol) in acetonitrile (80 mL). After 15 min, the reaction was concentrated. Purification by silica gel chromatography (100% hexanes→30% ethyl acetate/hexanes) gave the title compound (4.52 g).

Workup

  1. concentrationthe reaction was concentrated
  2. customPurification by silica gel chromatography (100% hexanes→30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-dc07df47e30a4c3595f1ab5b813b1004
Source dataset
uspto-grants-2009_02
Patent number
US07491713B2

Reaction notes

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