Isopropyl iodide → N-t-butyloxycarbonyl-alpha-isopropyl-beta-alanine t-butyl ester

Reaction equation

[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2].[CH:18](I)([CH3:20])[CH3:19]>>[C:1]([O:5][C:6](=[O:17])[CH:7]([CH:18]([CH3:20])[CH3:19])[CH2:8][NH:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 2

HCID 6362Isopropyl iodide

HCID 540966173-Tert-butoxycarbonylamino-propionic acid tert-butyl ester

Product 1

HCID 86753688N-t-butyloxycarbonyl-alpha-isopropyl-beta-alanine t-butyl esterYield 42%

Procedure

N-t-Butyloxycarbonyl-β-alanine t-butyl ester (2.0 g) was isopropylated by the same procedure as in Comparative Example 4-(1) using isopropyl iodide (1.8 ml) to yield an oil of N-t-butyloxycarbonyl-α-isopropyl-β-alanine t-butyl ester (990 mg, 42%).

Sources & evidence

ORD record: ord-a2736c7a52a24d8ba4a1a8f2bbefc422
Source dataset: uspto-grants-1999_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05866592

Reaction notes

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