1-(1,1-Dimethylethyl) hydrogen L-glutamate → (S)-5-(tert-butoxy)-5-oxo-4-(pent-4-enamido)pentanoic acid

HRID 1482185Notes

Reaction equation

HRID 1482185 reaction equation
[NH2:1][C@H:2]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3][CH2:4][C:5]([OH:7])=[O:6].N[C@H](C(OC(C)(C)C)=O)CC(O)=O.C(OC(=O)[C@@H](N[C:40](=[O:45])[CH2:41][CH2:42][CH:43]=[CH2:44])CC(O)=O)(C)(C)C>>[C:11]([O:10][C:8](=[O:9])[C@@H:2]([NH:1][C:40](=[O:45])[CH2:41][CH2:42][CH:43]=[CH2:44])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])([CH3:14])([CH3:13])[CH3:12]

Participants

4

Reactant 3

HCID 1175051-(1,1-Dimethylethyl) hydrogen L-glutamate2×HCID 7016377(3S)-3-amino-4-(tert-butoxy)-4-oxobutanoic acidHCID 89668326(S)-4-(tert-butoxy)-4-oxo-3-(pent-4-enamido)butanoic acid

Product 1

HCID 89668310(S)-5-(tert-butoxy)-5-oxo-4-(pent-4-enamido)pentanoic acid

Procedure

A mixed crude product B (9.28 g, 100%) of (S)-5-(tert-butoxy)-5-oxo-4-(pent-4-enamido)pentanoic acid (Compound 1b-II) and pent-4-enoic acid (1:0.8) was obtained using (S)-4-amino-5-(tert-butoxy)-5-oxopentanoic acid (Compound 1a-II, 5.00 g, 24.2 mmol) in place of (S)-3-amino-4-(tert-butoxy)-4-oxobutanoic acid (Compound 1a-I) under the same conditions as in the preparation example for Compound 1b-I.

Sources & evidence

ORD record
ord-75fa8f86aa454114ae80e2db297fd1e5
Source dataset
uspto-grants-2016_08
Patent number
US09409952B2

Reaction notes

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