Phenylacetic Acid → HCID 13631278, compound

HRID 279814Notes

Reaction equation

[NH2:1][C@H:2]1[CH2:5][N:4]([C:6]([NH:8][S:9]([NH2:12])(=[O:11])=[O:10])=[O:7])[C:3]1=[O:13].C1(N=C=NC2CCCCC2)CCCCC1.OC1C2N=NNC=2C=CC=1.[C:39]1([CH2:45][C:46](O)=[O:47])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>>[NH2:12][S:9]([NH:8][C:6]([N:4]1[CH2:5][C@H:2]([NH:1][C:46]([CH2:45][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[O:47])[C:3]1=[O:13])=[O:7])(=[O:10])=[O:11]

Participants

Reactant 4

HCID 999Phenylacetic Acid

HCID 10868Dicyclohexylcarbodiimide

HCID 54335182HCID 54335182, compound

HCID 178418300HCID 178418300, compound

Product 1

HCID 13631278HCID 13631278, compoundYield 34.1%

Conditions

Temperature: 0 °C

Procedure

(S)-3-Amino-N-(aminosulfonyl)-2-oxo-1-azetidinecarboxamide (see example 22, or prepared by hydrogenating 140 mg of (S)-N-(aminosulfonyl)-3-[[(phenylmethoxy)carbonyl]amino]-2-oxo-1-azetidinecarboxamide in dimethylformamide used 50 mg of 5% palladium on charcoal catalyst) was acylated with 100 mg of dicyclohexylcarbodiimide, 20 mg of hydroxybenzotriazole and 55 mg of benzeneacetic acid. The mixture was stirred at 0° C. for 6 hours and dicyclohexylurea was filtered off. Dimethylformamide was distilled off, the residue was dissolved in 5 ml of acetone and the solution was, after standing for about 16 hours, filtered and then evaporated. The crude material was chromatographed on an HP-20 column eluting with water/acetone (6:4) to give 45 mg of the title compound, melting point 137° C.

Workup

filtrationdicyclohexylurea was filtered off
distillationDimethylformamide was distilled off
dissolutionthe residue was dissolved in 5 ml of acetone
waitafter standing for about 16 hours
filtrationfiltered
customevaporated
customThe crude material was chromatographed on an HP-20 column
washeluting with water/acetone (6:4)

Sources & evidence

ORD record: ord-daf982ddd798446882c7a4a73a8262d4
Source dataset: uspto-grants-1986_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04587047

Reaction notes

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