Acetyl chloride → HCID 86679435, compound

HRID 1776483Notes

Reaction equation

HRID 1776483 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:49][CH2:50][CH2:51][OH:52])[C:20]([O:22][C@H:23]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]4[CH2:48][CH2:47]4)[CH:35]=3)[CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27][C:26]=3[Cl:33])=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:53](Cl)(=[O:55])[CH3:54]>C(Cl)Cl>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:49][CH2:50][CH2:51][O:52][C:53](=[O:55])[CH3:54])[C:20]([O:22][C@H:23]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]4[CH2:47][CH2:48]4)[CH:35]=3)[CH2:24][C:25]3[C:26]([Cl:33])=[CH:27][N+:28]([O-:32])=[CH:29][C:30]=3[Cl:31])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 86719335HCID 86719335, compound

Product 1

HCID 86679435HCID 86679435, compoundYield 100.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-((S)-2-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-5-hydroxypentanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-ethyl)-3,5-dichloropyridine 1-oxide (268 mg, 0.354 mmol) in DCM (5 mL), acetyl chloride (54 μl, 0.757 mmol) and TEA (108 μl, 0.775 mmol) were added. The mixture was stirred at RT for 3 hours. The mixture was then diluted with DCM and washed with NaHCO3 sat. sol., HCl 0.1 M and brine. The organic phase was dried over Na2SO4 and the solvent was evaporated, to yield 284 mg of the title compound.

Workup

  1. washwashed with NaHCO3 sat. sol., HCl 0.1 M and brine
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-73bee35b7e3d480aa6cdf206a6957e30
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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