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

HRID 1005790

Reaktionsgleichung

Reaktionsgleichung von HRID 1005790
[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].[C:23]([CH2:27][CH:28]=O)([CH3:26])([CH3:25])[CH3:24].C1CCN2C(=NCCC2)CC1>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3](=[O:4])[C:5]([NH:6][C:7]([O:9][CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:8])=[CH:28][CH2:27][C:23]([CH3:26])([CH3:25])[CH3:24]

Komponenten

6

Edukt 3

HCID 763353,3-DimethylbutanalHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2734718Methyl 2-{[(benzyloxy)carbonyl]amino}-2-(dimethyl phosphono)acetate

Produkt 1

HCID 694337082-Benzyloxycarbonylamino-5,5-dimethyl-hex-2-enoic acid methyl esterAusbeute 94,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

N-(Benzyloxycarbonyl)-α-phosphonoglycine trimethyl ester (2 g, 6.0 mmol, 1.0 equiv) was dissolved in dry THF (20 mL). tert-Butylacetaldehyde 90.758 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).

Aufarbeitung

  1. washwashed with 1×50 mL water, and 1×50 mL brine
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b16ea216671d456fb9fc93a283f39af6
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06787540B2

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