Hydrochloric Acid → HCID 9930514, compound

HRID 355434Notes

Reaction equation

HRID 355434 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([P:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.[NH2:30][OH:31].C[O-].[Na+].Cl>CO>[OH:31][NH:30][C:3](=[O:2])[CH2:4][N:5]([P:14]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 10500777HCID 10500777, compoundHCID 10942334Sodium Methoxide

Product 1

HCID 9930514HCID 9930514, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

N-(Diphenyl phosphinyl)-N-(2-phenylethyl)glycine methyl ester (160 mg, 0.41 mmol) is dissolved in methanol (2.5 mL). To this is added hydroxylamine hydrochloride (57 mg, 0.81 mmol), followed by a 2 mmol of a 25% methanolic solution of sodium methoxide. The reaction is stirred for 16 hours, neutralized with 1N hydrochloric acid and concentrated. The crude product is purified by silica gel flash chromatography to give 41.6 mg (26%) of N-hydroxy-2-[[diphenylphosphinyl](2-phenylethyl)-amino]-acetamide as a colorless solid: MS-IS m/z 395 [M+H]+, 417 [M+Na]+, 433 [M+K]+. (R1 =phenyl ethyl, R2 =H, R3 =phenyl, R4 =phenyl).

Workup

  1. concentrationconcentrated
  2. customThe crude product is purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-87f67cf898b44ad8887ed80891e654d2
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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