Acetyl chloride → HCID 59722689, compound

HRID 1664838Notes

Reaction equation

HRID 1664838 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[F:5][C:6]1[C:11]([F:12])=[CH:10][CH:9]=[CH:8][C:7]=1[C@H:13]1[CH2:19][N:18]2[C:20]([CH2:23][CH2:24][OH:25])=[CH:21][N:22]=[C:17]2[C@H:16]([NH:26][C:27](=[O:33])[O:28][C:29]([CH3:32])([CH3:31])[CH3:30])[CH2:15][CH2:14]1.C(N(CC)CC)C.C(=O)(O)[O-].[Na+]>ClCCl>[C:1]([O:25][CH2:24][CH2:23][C:20]1[N:18]2[CH2:19][C@H:13]([C:7]3[CH:8]=[CH:9][CH:10]=[C:11]([F:12])[C:6]=3[F:5])[CH2:14][CH2:15][C@@H:16]([NH:26][C:27]([O:28][C:29]([CH3:30])([CH3:32])[CH3:31])=[O:33])[C:17]2=[N:22][CH:21]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 59722595HCID 59722595, compound

Product 1

HCID 59722689HCID 59722689, compoundYield 82.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (24 μL, 0.344 mmol) was added to a solution of tert-butyl (6S,9R)-6-(2,3-difluorophenyl)-3-(2-hydroxyethyl)-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepin-9-ylcarbamate (70 mg, 0.172 mmol) and triethylamine (48 μL, 0.344 mmol) in dichloromethane (6 mL) at 0° C. After 1.5 h, saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (2×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol) gave the title compound (64 mg). MS 450.2 (M+1).

Workup

  1. extractionthe mixture was extracted with dichloromethane (2×)
  2. dry with materialThe combined organic extracts were dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification by silica gel chromatography (100% dichloromethane→95% dichloromethane/methanol)

Sources & evidence

ORD record
ord-46655f19fba340ce974f2c6213e87c68
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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