HCID 12735383, compound → (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-cyclopropyl-2-oxobut-3-enyl)carbamate

HRID 627269Notes

Reaction equation

HRID 627269 reaction equation
C1(/C(=N/NS(C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)(=O)=O)/C)CC1.[Si](OC[C@@H](N(CC(N(OC)C)=O)C(=O)OC(C)(C)C)C=C)(C(C)(C)C)(C)C.[Si:53]([O:60][CH2:61][C@@H:62]([N:65]([CH2:73][C:74](=[O:80])[C:75](=[CH2:79])[CH:76]([CH3:78])[CH3:77])[C:66](=[O:72])[O:67][C:68]([CH3:71])([CH3:70])[CH3:69])[CH:63]=[CH2:64])([C:56]([CH3:59])([CH3:58])[CH3:57])([CH3:55])[CH3:54]>>[Si:53]([O:60][CH2:61][C@@H:62]([N:65]([CH2:73][C:74](=[O:80])[C:75]([CH:76]1[CH2:77][CH2:78]1)=[CH2:79])[C:66](=[O:72])[O:67][C:68]([CH3:69])([CH3:70])[CH3:71])[CH:63]=[CH2:64])([C:56]([CH3:59])([CH3:57])[CH3:58])([CH3:55])[CH3:54]

Participants

4

Reactant 3

HCID 12735383HCID 12735383, compound2×HCID 89855339(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate2×HCID 131735279(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(4-methyl-3-methylene-2-oxopentyl)carbamate

Product 1

HCID 89852359(S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(3-cyclopropyl-2-oxobut-3-enyl)carbamate

Procedure

The title compound was prepared from (E)-N′-(1-cyclopropylethylidene)-2,4,6-triisopropylbenzenesulfonohydrazide (Intermediate 261, 17.58 g, 48.22 mmol) and (S)-tert-butyl 1-(tert-butyldimethylsilyloxy)but-3-en-2-yl(2-(methoxy(methyl)amino)-2-oxoethyl)carbamate (Intermediate 5, 9.71 g, 24.11 mmol) following the procedure described for Intermediate 34. The desired product was obtained as a light yellow oil (4.86 g, 49%).

Sources & evidence

ORD record
ord-441d22e938ea4befbd0f14c20f14fe60
Source dataset
uspto-grants-2016_04
Patent number
US09309245B2

Reaction notes

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