L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]- → 1,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamate

HRID 52203

Reaction equation

HRID 52203 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([OH:19])=O)[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:21][NH:22][O:23][CH3:24]>>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:17]([N:22]([CH3:21])[O:23][CH3:24])=[O:19])[CH2:10][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

3

Reactant 2

HCID 77857L-Phenylalanine, N-[(1,1-dimethylethoxy)carbonyl]-HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

Product 1

HCID 110559451,1-Dimethylethyl N-((1S)-2-(methoxymethylamino)-2-oxo-1-(phenylmethyl)ethyl)carbamateYield 8,042.2%

Procedure

The title compound was synthesized from tert-butyloxycarbonyl-L-phenylalanine (2.65 g, 0.1 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.07 g, 11 mmol) according to the procedure given for 1. The synthesis yielded compound 5 as an oil (2.48 g, 81%): Rf 0.40 (ethyl acetate/hexane, 1:1), Rf 0.78 (chloroform/methanol/acetic acid, 85:10:5); 1H-NMR (CDCl3, 17° C.)δ 1.38 (9H, s, C(CH3)3, 3.05 (2H, m, CH2), 3.18 (3H, s, N--CH3),3.66 (3 H, s, O--CH3), 4.97 (1H, m, CH), 5.18 (1H, d (br.),NH), 7.17-7.28 (5H, m, C6H5).

Sources & evidence

ORD record
ord-c99631c59dbc425dab03627caac5bade
Source dataset
uspto-grants-1997_04
Patent number
US05616605

Linked notes

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