Diisopropylethylamine → HCID 178501876, compound

HRID 490948Notes

Reaction equation

HRID 490948 reaction equation
[CH3:1][O:2][C:3](=[O:38])[CH:4]([C:14]1[CH:19]=[CH:18][CH:17]=[C:16]([NH:20][C:21]([NH:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:15]=1)[O:5][P:6]([CH:9]([NH2:13])[CH:10]([CH3:12])[CH3:11])([OH:8])=[O:7].CCN(C(C)C)C(C)C.[C:48]1([CH:54]=[CH:55][S:56](Cl)(=[O:58])=[O:57])[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1>C(Cl)Cl>[C:26]([O:25][C:23]([N:22]=[C:21]([NH:30][C:31]([O:33][C:34]([CH3:36])([CH3:35])[CH3:37])=[O:32])[NH:20][C:16]1[CH:15]=[C:14]([CH:4]([O:5][P:6]([CH:9]([NH:13][S:56]([CH:55]=[CH:54][C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)(=[O:58])=[O:57])[CH:10]([CH3:12])[CH3:11])([OH:8])=[O:7])[C:3]([O:2][CH3:1])=[O:38])[CH:19]=[CH:18][CH:17]=1)=[O:24])([CH3:28])([CH3:29])[CH3:27]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 107500Ethenesulfonyl chloride, 2-phenyl-HCID 178501873HCID 178501873, compound

Product 1

HCID 178501876HCID 178501876, compoundYield 57.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid methyl ester (300 mg, 0.53 mmol) in 8 mL methylene chloride was added DIEA (0.44 mL, 1.06 mmol), which was cooled to 0° C. by an ice-water bath. Then a solution of 2-phenylethenylsulfonyl chloride (120 mg, 0.59 mmol) in 1 mL methylene chloride was added dropwise. The resulting mixture was stirred at ambient temperature for thirty minutes. The mixture was washed with water, 2N NaHSO4, and brine. The organic phase was dried over sodium sulfate and concentrated to afford a yellow solid. Purification by chromatograph on silica gel afforded a yellow solid, 2-(3-(N′,N″-di(t-butoxycarbonyl)guanidino)phenyl)-2-((1-(2-phenylethenylsulfonyl)amino-2-methylpropyl)(hydroxy)phosphinoyloxy)ethanoic acid, methyl ester, (220 mg).

Workup

  1. washThe mixture was washed with water, 2N NaHSO4, and brine
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customto afford a yellow solid
  5. customPurification by chromatograph on silica gel

Sources & evidence

ORD record
ord-8ffea9762e84452086d31dcc4ef1312d
Source dataset
uspto-grants-2009_05
Patent number
US07528173B2

Reaction notes

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