Isopropanol → HCID 53641585, compound

HRID 1448426Notes

Reaction equation

[CH:1]([OH:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[F:12][C:13]([F:31])([F:30])[C:14]([N:16]([CH2:23][P:24]([O:28]Cl)([O:26]Cl)=[O:25])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15].[C:32]1([SH:38])[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1>CCOCC>[F:12][C:13]([F:31])([F:30])[C:14]([N:16]([CH:23]([O:4][CH:1]([CH3:3])[CH3:2])[P:24]([OH:28])([O:26][S:38][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:25])[CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:15]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of isopropanol (2.9 ml, 0.038 mole) and triethylamine (5.3 ml, 0.038 mole) in 50 ml. of ether was added to a solution of ethyl N-trifluoroacetyl-N-(dichlorophosphonomethyl)glycinate (13.2 g, 0.04 mole) in 150 ml. of ether at 0° C. After three hours, the solution was filtered and the cooled (0° C.) filtrate was treated with a solution of thiophenol (3.9 ml, 0.038 mole) and triethylamine (5.3 ml, 0.038 mole) in 50 ml. of ether. The resulting mixture was stirred at 25° C. for 16 hours, then filtered. The filtrate was washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution, then concentrated in vacuo. The residual oil was chromatographed on silica gel eluting with ethyl acetate/cyclohexane (6:4) to afford ethyl N-trifluoroacetyl-N-(isopropoxy(phenylthio)phosphonomethyl)glycinate (7.7 g) as a light yellow oil, ND25 =1.4951.

Workup

customat 0° C
filtrationthe solution was filtered
filtrationfiltered
washThe filtrate was washed with 3% hydrochloric acid, 3% ammonium hydroxide and saturated sodium chloride solution
concentrationconcentrated in vacuo
customThe residual oil was chromatographed on silica gel eluting with ethyl acetate/cyclohexane (6:4)

Sources & evidence

ORD record: ord-fd1cad44200f490094e9de989a8580c9
Source dataset: uspto-grants-1979_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04180394

Reaction notes

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