Ethylmorpholine → 2'-Isobutyl-4-methylvalerohydrazide

HRID 1979208Notes

Reaction equation

C(N[C@H](C(O)=O)C)(=O)C.C(N1CCOCC1)C.ClC(OCC(C)C)=O.O1CCCCC1ONC([C@H]([C@@H:46]([CH2:55][CH:56]([CH3:58])[CH3:57])[C:47]([NH:49][NH:50][CH2:51][CH:52]([CH3:54])[CH3:53])=[O:48])C/C=C/C1C=CC=CC=1)=O>O1CCCC1.C(OCC)(=O)C>[CH2:51]([NH:50][NH:49][C:47](=[O:48])[CH2:46][CH2:55][CH:56]([CH3:58])[CH3:57])[CH:52]([CH3:54])[CH3:53]

Participants

Conditions

Temperature: 10 °C

Procedure

A solution of 0.144 g of N-acetyl-L-alanine in 10 ml tetrahydrofuran was cooled to −10° C. and treated with 0.140 ml of N-ethylmorpholine and 0.143 ml of isobutyl chloroformate. The mixture was stirred for a further 10 minutes at 10° C. and then treated with 0.459 g of (E)-2(R)-[1(S)-[(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide. The mixture was allowed to warm to 0° C. and stirring was continued for 1.5 hours. The mixture was then diluted with ethyl acetate and washed in sequence with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and brine. Drying over magnesium sulphate and evaporation gave 0.601 g of (E)-2′-(N-acetyl-L-alanyl)-2(R)-[1(S)-(tetrahydro-2(RS)-pyranyloxy)carbamoyl]-4-phenyl-3-butenyl]-2′-isobutyl-4-methylvalerohydrazide in the form of a white solid.

Workup

temperatureto warm to 0° C.
stirringstirring
waitwas continued for 1.5 hours
washwashed in sequence with 5% aqueous citric acid, 5% aqueous sodium hydrogen carbonate and brine
dry with materialDrying over magnesium sulphate and evaporation

Sources & evidence

ORD record: ord-7af4cba39412418bbcbe6c73fcc93180
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06239151B1

Reaction notes

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