Triethylamine → n-((5s)-3-(4-(1-Cyano-2s-(pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

HRID 395569Notes

Reaction equation

HRID 395569 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[S:7][CH2:8][CH:9]1[CH:13]=[C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)[CH2:11][NH:10]1.[CH2:31]([N:33](CC)CC)C.N#CBr>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:31]([N:10]1[CH2:11][C:12]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:27](=[O:29])[CH3:28])[O:22][C:21]3=[O:30])=[CH:16][CH:15]=2)=[CH:13][CH:9]1[CH2:8][S:7][C:2]1[N:3]=[CH:4][CH:5]=[CH:6][N:1]=1)#[N:33]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 10476Cyanogen BromideHCID 69998857n-((5s)-3-(4-(2s-(Pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamide

Product 1

HCID 88095695n-((5s)-3-(4-(1-Cyano-2s-(pyrimidin-2-yl)thiomethyl-2,5-dihydropyrrol-4-yl)phenyl)-2-oxooxazolidin-5-ylmethyl)acetamideYield 66%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent3×

Procedure

The amine (Reference Example 7, 0.103 g, 0.24 mM) in CH2Cl2 (4 ml) was treated with triethylamine (0.073 g, 0.100 ml, 0.72 mM) and 4-dimethylaminopyridine (4-DMAP) (0.003 g, 0.024 mM), followed by a suspension of cyanogen bromide (0.129 g, 1.21 mM) in CH2Cl2 (3 ml). The solution was stirred for 1 hour. The mixture was then diluted with CH2Cl2 (7 ml), washed with sat. aq. NaHCO3 (3 ml), water (3 ml), dried and evaporated to an oil which was purified by Isolute chromatography (using as eluant 6% MeOH/CH2Cl2). The resultant oil was triturated with diethyl ether to give the title product (0.071 g, 66%).

Workup

  1. washwashed with sat. aq. NaHCO3 (3 ml), water (3 ml)
  2. customdried
  3. customevaporated to an oil which
  4. customwas purified by Isolute chromatography (using as eluant 6% MeOH/CH2Cl2)
  5. customThe resultant oil was triturated with diethyl ether

Sources & evidence

ORD record
ord-9883aa48abb64622ac062a5ef490fcdd
Source dataset
uspto-grants-2003_08
Patent number
US06605630B1

Reaction notes

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