Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate → HCID 66843543, compound

HRID 2193860Notes

Reaction equation

[CH3:1][O:2][C:3]([CH:5](P(OC)(OC)=O)[NH:6][C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:8])=[O:4].CC(C)([O-])C.[K+].[CH2:29]([O:31][P:32]([CH3:37])([CH2:34][CH:35]=O)=[O:33])[CH3:30]>C(Cl)Cl>[CH2:10]([O:9][C:7]([NH:6]/[C:5](=[CH:35]\[CH2:34][P:32]([O:31][CH2:29][CH3:30])([CH3:37])=[O:33])/[C:3]([O:2][CH3:1])=[O:4])=[O:8])[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

Conditions

Temperature: -78 °C

Procedure

After 214 mg of N-(benzyloxycarbonyl)-alpha-phosphonoglycine trimethyl ester was dissolved in 5 ml of methylene chloride, 74 mg of potassium t-butoxide was added, followed by stirring at −78° C. for 30 minutes. 76.5 mg of 2-(ethoxy(methyl)phosphinyl)-acetaldehyde in methylene chloride solution (1 ml) was gradually added dropwise into this reaction solution, which was stirred for 1 hour. After the reaction temperature was gradually raised up to room temperature, further the reaction solution was stirred for 3 hours. Consuming of ingredients was confirmed by using TLC, and the solvent was removed off under reduced pressure. The residual was purified by silica gel column chromatography (chloroform-methanol (100:1-50:1)), 168 mg of an objective compound was obtained (93% yield).

Workup

stirringwas stirred for 1 hour
temperatureAfter the reaction temperature was gradually raised up to room temperature
stirringfurther the reaction solution was stirred for 3 hours
customConsuming of ingredients
customthe solvent was removed off under reduced pressure
customThe residual was purified by silica gel column chromatography (chloroform-methanol (100:1-50:1))

Sources & evidence

ORD record: ord-61170ebdfa9f4188b679e20114d2eb2b
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329935B2

Reaction notes

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