Methylamine hydrochloride → tert-butyl N-[2-hydroxy-2-methyl-1-(methylcarbamoyl)propyl]carbamate

Reaction equation

[C:1]([O:5][C:6]([NH:8][CH:9]([C:13]([OH:16])([CH3:15])[CH3:14])[C:10](O)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:18][NH2:19]>>[OH:16][C:13]([CH3:15])([CH3:14])[CH:9]([NH:8][C:6](=[O:7])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[C:10](=[O:11])[NH:19][CH3:18]

Participants

Reactant 2

HCID 6364545Methylamine hydrochloride

HCID 13756005N-Boc-(+-)-2-amino-3-hydroxy-3-methylbutanoic acid

Product 1

HCID 90203567tert-butyl N-[2-hydroxy-2-methyl-1-(methylcarbamoyl)propyl]carbamate

Procedure

The title compound was synthesized in analogy to Example 112e, using 2-tert-Butoxycarbonylamino-3-hydroxy-3-methyl-butyric acid (CAN 105504-72-1) and methanamine hydrochloride as starting materials and isolated (486 mg, 38%); MS (ESI, m/z): 247.2 (M+H+).

Workup

customisolated (486 mg, 38%)

Sources & evidence

ORD record: ord-4d8a2040576f40389348dad3e3507555
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409866B2

Reaction notes

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