Hydrogen Bromide → HCID 72737701, compound

HRID 628128Notes

Reaction equation

HRID 628128 reaction equation
[BrH:1].[CH3:2][O:3][CH2:4][C@H:5]([NH:30][C:31]([C:33]1[S:37][C:36]([CH3:38])=[N:35][CH:34]=1)=[O:32])[C:6]([NH:8][C@@H:9]([CH2:27][O:28][CH3:29])[C:10]([NH:12][C@@H:13]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:14]([C@@:16]1([CH3:19])[CH2:18][O:17]1)=[O:15])=[O:11])=[O:7]>O1CCOCC1.C(Cl)Cl>[Br:1][CH2:18][C@:16]([OH:17])([CH3:19])[C:14](=[O:15])[C@@H:13]([NH:12][C:10](=[O:11])[C@@H:9]([NH:8][C:6](=[O:7])[C@@H:5]([NH:30][C:31]([C:33]1[S:37][C:36]([CH3:38])=[N:35][CH:34]=1)=[O:32])[CH2:4][O:3][CH3:2])[CH2:27][O:28][CH3:29])[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 260Hydrogen BromideHCID 25067547O-Methyl-N-((2-methylthiazol-5-yl)carbonyl)-L-seryl-O-methyl-N-((1S)-1-benzyl-2-((2R)- 2-methyloxiran-2-yl)-2-oxoethyl)-L-serinamide

Product 1

HCID 72737701HCID 72737701, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Hydrobromic acid (2 eq., 0.314 mL) was added to N—((S)-3-methoxy-1-(((S)-3-methoxy-1-(((S)-1-((R)-2-methyloxiran-2-yl)-1-oxo-3-phenylpropan-2-yl)amino)-1-oxopropan-2-yl)amino)-1-oxopropan-2-yl)-2-methylthiazole-5-carboxamide (1.0 g, 1.88 mmol) in dioxane (20 mL) at 0° C., the reaction allowed to warm to room temperature and stirred overnight. The mixture was diluted with DCM, washed with aqueous saturated sodium bicarbonate, brine, dried (Na2SO4) and evaporated. The residue was purified by Biotage flash column chromatography to give product as a white solid (0.722 g, 48%); 1H NMR (CDCl3): δ 8.06(s, 1H), 7.28-7.18 (m, 6H), 7.02 (d, J=7.6 Hz, 1H), 6.85 (d, J=6.4 Hz, 1H), 5.45-5.40 (m, 1H), 4.71-4.66(m, 1H), 4.53-4.48 (m, 1H), 4.20 (s, 1H), 3.85-3.75 (m, 3H), 3.57-3.52 (m, 2H), 3.44-3.39 (m, 4H), 3.31 (s, 3H), 3.23-3.18 (m, 1H), 2.94-2.89 (m, 1H), 2.75 (s, 3H), 1.18 (s, 3H); MS for C25H33BrN4O7S m/z 614 (M+H)+.

Workup

  1. washwashed with aqueous saturated sodium bicarbonate, brine
  2. dry with materialdried (Na2SO4)
  3. customevaporated
  4. customThe residue was purified by Biotage flash column chromatography

Sources & evidence

ORD record
ord-b094ba1f19ac403dac7d460c3231d554
Source dataset
uspto-grants-2016_04
Patent number
US09309283B2

Reaction notes

Loading…