Acetyl chloride → HCID 67061843, compound

HRID 910803Notes

Reaction equation

HRID 910803 reaction equation
[CH3:1][O:2][CH2:3][C@H:4]([CH3:51])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:39])=[O:38])[C@H:16]([CH2:47][CH:48]([NH2:50])[CH3:49])[CH2:15]2)=[CH:10][CH:9]=1.CCN(CC)CC.[C:59](Cl)(=[O:61])[CH3:60]>C(Cl)Cl.O>[CH3:1][O:2][CH2:3][C@H:4]([CH3:51])[CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C@@H:14]2[C@@H:19]([O:20][CH2:21][C:22]3[CH:23]=[CH:24][C:25]4[O:30][CH2:29][CH2:28][N:27]([CH2:31][CH2:32][CH2:33][O:34][CH3:35])[C:26]=4[CH:36]=3)[CH2:18][N:17]([S:37]([C:40]3[CH:45]=[CH:44][C:43]([CH3:46])=[CH:42][CH:41]=3)(=[O:38])=[O:39])[C@H:16]([CH2:47][C@H:48]([NH:50][C:59](=[O:61])[CH3:60])[CH3:49])[CH2:15]2)=[CH:10][CH:9]=1

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86651708HCID 86651708, compound

Product 1

HCID 67061843HCID 67061843, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.0 mmol of (R and S)-2-[(2S,4R,5R)-4-[4-((S)-3-methoxy-2-methyl-propoxymethyl)-phenyl]-5-[4-(3-methoxy-propyl)-3,4-dihydro-2H-benzo[1,4]oxazin-6-ylmethoxy]-1-(toluene-4-sulfonyl)-piperidin-2-yl]-1-methyl-ethylamine, 4.0 mmol of Et3N in 25 ml of CH2Cl2 are added 2.0 mmol of acetyl chloride at 0° C. and the resulting mixture is stirred for 1 h. The reaction mixture is diluted with water and extracted with CH2Cl2. The organic phases are combined, dried over Na2SO4 and concentrated under reduced pressure. The resulting diastereomeric mixture is separated by flash chromatography (SiO2 60 F) to afford:

Workup

  1. extractionextracted with CH2Cl2
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting diastereomeric mixture is separated by flash chromatography (SiO2 60 F)
  5. customto afford

Sources & evidence

ORD record
ord-5a73ac2af7184123a000e3c78d029953
Source dataset
uspto-grants-2011_09
Patent number
US08022068B2

Reaction notes

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