Acetyl chloride → HCID 67206295, compound

HRID 2041714Notes

Reaction equation

HRID 2041714 reaction equation
[C:1]1([CH2:7][O:8][C:9](=[O:41])[N:10]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]3[CH:20]=[C:21]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29](=[O:31])[CH3:30])[C@@H:24]([CH3:32])[CH2:23][C@H:22]4[NH:33]C(OC(C)(C)C)=O)=[CH:15][CH:14]=2)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C>CO>[C:29]([N:25]1[C:26]2[C:21](=[CH:20][C:19]([C:16]3[CH:17]=[CH:18][C:13]([CH2:12][N:10]([CH3:11])[C:9](=[O:41])[O:8][CH2:7][C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)=[CH:14][CH:15]=3)=[CH:28][CH:27]=2)[C@H:22]([NH2:33])[CH2:23][C@@H:24]1[CH3:32])(=[O:31])[CH3:30]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 67207638HCID 67207638, compound

Product 1

HCID 67206295HCID 67206295, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of phenylmethyl({4-[(2S,4R)-1-acetyl-4-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}methyl)methylcarbamate (for a preparation see intermediate 81) (1 g, 1.793 mmol) in methanol (50 mL) was added acetyl chloride (2 mL, 28.1 mmol). The resulting mixture was stirred at room temperature for 3 h then concentrated in vacuovacuo. The residue was loaded on a 50 g SCX column, then eluted with MeOH (3 column volume (CV)) followed by 2N NH3 in methanol (4 CV). The ammonia fractions were combined and evaporated in vacuovacuo. Purification of the residue obtained by flash chromatography on silica gel (40 g column, gradient:0 to 5% (2N NH3 in MeOH) in DCM) gave phenylmethyl ({4-[(2S,4R)-1-acetyl-4-amino-2-methyl-1,2,3,4-tetrahydro-6-quinolinyl]phenyl}methyl)methylcarbamate (581 mg, 1.27 mmol, 71%) as a colourless oil which solidified on standing.

Workup

  1. concentrationthen concentrated in vacuovacuo
  2. washeluted with MeOH (3 column volume (CV))
  3. customevaporated in vacuovacuo
  4. customPurification of the residue
  5. customobtained by flash chromatography on silica gel (40 g column, gradient:0 to 5% (2N NH3 in MeOH) in DCM)

Sources & evidence

ORD record
ord-fc7668ceaf434ba88052462476315243
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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