(2S)-2-Amino-N,N-dimethyl-3-phenylpropanamide hydrochloride → HCID 178484518, compound

HRID 651196Notes

Reaction equation

HRID 651196 reaction equation
Cl.[NH2:2][C@@H:3]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[Cl:16][C:17]1[CH:28]=[CH:27][C:20]2[NH:21][C:22]([C:24](O)=[O:25])=[N:23][C:19]=2[CH:18]=1>>[CH3:7][N:6]([CH3:8])[C:4]([CH:3]([NH:2][C:24]([C:22]1[NH:21][C:20]2[CH:27]=[CH:28][C:17]([Cl:16])=[CH:18][C:19]=2[N:23]=1)=[O:25])[CH2:9][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[O:5]

Participants

3

Reactant 2

HCID 12653778(2S)-2-Amino-N,N-dimethyl-3-phenylpropanamide hydrochlorideHCID 178524849HCID 178524849, compound

Product 1

HCID 178484518HCID 178484518, compound

Procedure

(S)-2-Amino-N,N-dimethyl-3-phenyl-propionamide hydrochloride (2.0 mmol) and 5-chloro-1H-benzoimidazole-2-carboxylic acid (Crowther et al., J. Chem. Soc. 1949, p.1268, 2.0 mmol) were coupled according to Procedure A and the product purified by chromatography on silica gel eluted with 1:1 ethyl acetate-hexanes (235 mg, 63%): HPLC (60/40) 4.92 min (91%); PBMS 371/373 (MH+, 100%); 1H NMR (CDCl3) δ11.25 (br, 0.6H), 10.9 (br, 0.4H), 8.36 (m, 1H), 7.78 (d, 0.4H, J=7.72 (d, 0.6H, J=8.8 Hz), 7.52 (d, 0.6H, J=2 Hz), 7.41 (d, 0.4H, J=8.4 Hz), 7.35-7.1 (m, 6H), 7.35 (m, 1H), 3.16 (m, 2H), 2.90 (s, 3H), 2.68 (s, ca. 2H), 2.67 (s, ca. 1H).

Workup

  1. customthe product purified by chromatography on silica gel
  2. washeluted with 1:1 ethyl acetate-hexanes (235 mg, 63%)
  3. custom(60/40) 4.92 min (91%)

Sources & evidence

ORD record
ord-fd935494c8134807baf5f4cf494f4292
Source dataset
uspto-grants-2001_08
Patent number
US06277877B1

Reaction notes

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