Tert-butyl 3-(methylamino)propanoate → tert-butyl N-(3-cyano-5-fluorobenzyl)-methyl-beta-alaninate

HRID 2404303Notes

Reaction equation

HRID 2404303 reaction equation
BrCC1C=C(C=C(F)C=1)C#N.N[C:13](=[N:32]O)[C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:17][N:18]([CH3:27])[CH2:19][C:20](OC(C)(C)C)=O.CNCC[C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39]>>[C:13]([C:14]1[CH:15]=[C:16]([CH:28]=[C:29]([F:31])[CH:30]=1)[CH2:17][N:18]([CH3:27])[CH2:19][CH2:20][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])#[N:32]

Participants

4

Reactant 3

HCID 14760311Tert-butyl 3-(methylamino)propanoateHCID 666526293-(Bromomethyl)-5-fluorobenzonitrileHCID 76685333tert-butyl N-{3-[amino(hydroxyimino)methyl]-5-fluorobenzyl}-N-methylglycinate

Product 1

HCID 66678645tert-butyl N-(3-cyano-5-fluorobenzyl)-methyl-beta-alaninate

Procedure

The title compound was prepared according the general procedure 10, starting from 3-(bromomethyl)-5-fluorobenzonitrile (Intermediate 24 Step 1, 750 mg, 3.5 mmol) and tert-butyl N-methyl-beta-alaninate (670 mg, 4.2 mmol, prepared as described in Biorg. Med. Chem. (11) 2003, 3083-3099). It was isolated as a pale yellow oil. 1H NMR (DMSO-d6, 300 MHz) δ 7.73 (ddd, J=8.6, 2.6, 1.4 Hz, 1H), 7.61 (s, 1H), 7.56-7.45 (m, 1H), 3.53 (s, 2H), 2.60 (t, J=6.7 Hz, 2H), 2.38 (t, J=6.7 Hz, 2H), 2.12 (s, 3H), 1.40 (s, 9H). LC/MS (Method B): 293.3 (M+H)+. HPLC (Method A) Rt 2.61 min (Purity: 96.2%).

Workup

  1. customIt was isolated as a pale yellow oil

Sources & evidence

ORD record
ord-9ca1f40d0e8a41e8bf0dc6c6e4c74f51
Source dataset
uspto-grants-2014_08
Patent number
US08802704B2

Reaction notes

Loading…