Dichloroacetyl chloride → HCID 15887433, compound

HRID 1740156Notes

Reaction equation

HRID 1740156 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH2:26])[O:22][C:21]3=[O:27])=[CH:16][C:15]=2[F:28])[CH2:10][CH2:9]1)=[O:7])([CH3:4])[CH3:3].C(N(CC)CC)C.[Cl:36][CH:37]([Cl:41])[C:38](Cl)=[O:39]>C(Cl)Cl>[CH3:4][C:2]([O:5][C:6]([N:8]1[CH2:9][CH2:10][CH:11]([C:14]2[CH:19]=[CH:18][C:17]([N:20]3[CH2:24][C@H:23]([CH2:25][NH:26][C:38](=[O:39])[CH:37]([Cl:41])[Cl:36])[O:22][C:21]3=[O:27])=[CH:16][C:15]=2[F:28])[CH2:12][CH2:13]1)=[O:7])([CH3:1])[CH3:3]

Participants

5

Reactant 3

HCID 6593Dichloroacetyl chlorideHCID 8471TriethylamineHCID 54424107HCID 54424107, compound

Product 1

HCID 15887433HCID 15887433, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of (S)-(-)-4-[4-[5-(aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperdinecarboxylic acid 1,1-dimethylethyl ester (EXAMPLE 20, Step 8, 400 mg) in dry methylene chloride (4.1 mL) at 0° C. under N2 is treated with triethylamine (0.21 mL) and dichloroacetyl chloride (0.11 mL), and the resulting mixture is stirred at 0° C. for three hours, diluted with methylene chloride (10 mL), washed with water (10 mL), saturated aqueous sodium bicarbonate (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which is then chromatographed on silica gel (70-230 mesh, 50 g), eluting with methanol/chloroform (5/95). Pooling and concentration of those fractions with an Rf =0.53 by TLC (methanol/chloroform, 10/90), trituration with methylene chloride/diethyl ether and filtration gives the title compound, mp 168-170° C.

Workup

  1. washwashed with water (10 mL), saturated aqueous sodium bicarbonate (10 mL) and saline (10 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customto give the crude product which
  5. customis then chromatographed on silica gel (70-230 mesh, 50 g)
  6. washeluting with methanol/chloroform (5/95)
  7. filtrationPooling and concentration of those fractions with an Rf =0.53 by TLC (methanol/chloroform, 10/90), trituration with methylene chloride/diethyl ether and filtration

Sources & evidence

ORD record
ord-b8926a31ff8842eaabcb9703f6edfefb
Source dataset
uspto-grants-1999_10
Patent number
US05968962

Reaction notes

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