2-(((Tert-butoxy)carbonyl)amino)butanoic acid → methyl N-{2-[(tert-butoxycarbonyl)amino]butanoyl}alaninate

HRID 1612319Notes

Reaction equation

HRID 1612319 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:11]([NH:13][CH:14]([CH:19]1CC1)[C:15]([O:17][CH3:18])=[O:16])=[O:12])[CH3:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:22](NC(CC)C(O)=O)(OC(C)(C)C)=O.Cl.NC(CC)C(OC)=O>>[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:10][CH3:22])[C:11]([NH:13][C@H:14]([C:15]([O:17][CH3:18])=[O:16])[CH3:19])=[O:12])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 3

HCID 3335222-(((Tert-butoxy)carbonyl)amino)butanoic acidHCID 13283515Methyl 2-aminobutanoate hydrochlorideHCID 58583288methyl{[N-(tert-butoxycarbonyl)-L-alanyl]amino}(cyclopropyl)acetate

Product 1

HCID 86588879methyl N-{2-[(tert-butoxycarbonyl)amino]butanoyl}alaninate

Procedure

Following the procedure for the preparation of methyl {[N-(tert-butoxycarbonyl)-L-alanyl]amino}(cyclopropyl)acetate but substituting N-Boc-alpha-aminobutyric acid and methyl 2-aminobutanoate hydrochloride and making non-critical variations provided the title compound as a solid: 1H NMR (CDCl3) δ 0.82-0.91, 1.24-1.38, 1.52, 1.68-2.05, 3.75, 4.20, 4.52-4.59, 5.05, 6.69.

Sources & evidence

ORD record
ord-643426b83b8640e6a0b606db6d9fbba1
Source dataset
uspto-grants-2006_01
Patent number
US06992087B2

Reaction notes

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