Acetyl chloride → HCID 137329922, compound

HRID 2428098Notes

Reaction equation

HRID 2428098 reaction equation
[C:1](Cl)([CH3:3])=[O:2].[C:5]([SiH2:9][O:10][C:11]([CH3:22])([CH3:21])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15][NH2:16])([CH3:8])([CH3:7])[CH3:6].CCN(C(C)C)C(C)C>C(Cl)Cl>[C:5]([SiH2:9][O:10][C:11]([CH3:22])([CH3:21])[C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][C:19]=1[Cl:20])[CH2:15][NH:16][C:1](=[O:2])[CH3:3])([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 1373299203-(tert-Butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine

Product 1

HCID 137329922HCID 137329922, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

AcCl (0.547 mL, 7.70 mmol) was added to a sol. of 3-(tert-butyl-dimethyl-silanyloxymethyl)-4-chloro-benzylamine (2.00 g, 7.00 mmol) and DIPEA (4.80 mL, 28.0 mmol) in CH2Cl2 (70 mL) at 0° C. The mixture was stirred for 1 h while warming up to rt. CH2Cl2 (30 mL) was added, and the mixture was washed with aq. sat. NH4Cl (2×), aq. 1M NaOH (1×) and brine (1×). The org. layer was dried over MgSO4, filtered, and the solvents were removed under reduced pressure. Purification of the crude by FC (EtOAc/heptane 60:40) yielded the title compound (2.10 g, 91%). LC-MS: tR=1.07 min; ES+: 369.19.

Workup

  1. washthe mixture was washed with aq. sat. NH4Cl (2×), aq. 1M NaOH (1×) and brine (1×)
  2. dry with materiallayer was dried over MgSO4
  3. filtrationfiltered
  4. customthe solvents were removed under reduced pressure
  5. customPurification of the crude by FC (EtOAc/heptane 60:40)

Sources & evidence

ORD record
ord-faff6c9fa06c4970bd6dcf1c8306bf21
Source dataset
uspto-grants-2011_06
Patent number
US07968720B2

Reaction notes

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