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HRID 1060659Erstellt: 27. Oktober 2026

3,3-Dimethylbutanal → 2-Benzyloxycarbonylamino-5,5-dimethyl-hex-2-enoic acid methyl ester

https://huagongshe.com/reaction/1060659

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt3,3-DimethylbutanalHCID 76335—
Edukt1,8-Diazabicyclo(5.4.0)undec-7-eneHCID 81184—
EduktMethyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetateHCID 2734718—
LösungsmittelDichloromethaneHCID 6344—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt2-Benzyloxycarbonylamino-5,5-dimethyl-hex-2-enoic acid methyl esterHCID 6943370894,4%

Reaktionsschritte

N-(Benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (2 g, 6.0 mmol, 1.0 equiv) was dissolved in dry THF (20 mL). tert-Butylacetaldehyde (0.758 mL, 6.0 mmol, 1.0 equiv) and DBU (0.903 mL, 6.0 mmol, 1.0 equiv) were added and the reaction mixture was stirred for 16 h. The solution was diluted with 100 mL of CH2Cl2 and washed with 1×50 mL water, and 1×50 mL brine. The organic layer was dried over Na2SO4, decanted and concentrated in vacuo to provide 2-benzyloxycarbonylamino-5,5-dimethyl-hex-2-enoic acid methyl ester as a thick oil (1.73 g, 94%) which was used without further purification; MS: 306 (M+1).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06525052B2
Quelldatensatzuspto-grants-2003_02
ORD IDord-d72b7a84bb3d4ffca02c6e298284073a
Quellennotizuspto-grants-2003_02