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

HRID 1824234Notes

Reaction equation

HRID 1824234 reaction equation
[CH3:1][O:2][C:3](=[O:21])[CH:4]([NH:8][C:9](=[O:20])[C@H:10]([CH3:19])[NH:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH:5]1CC1.[C:22](NC(CC)C(O)=O)(OC(C)(C)C)=O.Cl.NC(CC)C(OC)=O>>[C:15]([O:14][C:12]([NH:11][CH:10]([CH2:19][CH3:22])[C:9]([NH:8][C@H:4]([C:3]([O:2][CH3:1])=[O:21])[CH3:5])=[O:20])=[O:13])([CH3:16])([CH3:17])[CH3:18]

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-ebc1d4e1101743fa9cb61b75551fb7f9
Source dataset
uspto-grants-2006_05
Patent number
US07041672B2

Reaction notes

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