Acetyl chloride → HCID 18715614, compound

HRID 840415Notes

Reaction equation

HRID 840415 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[C:5]([OH:17])(=[O:16])[CH2:6][C:7]([CH2:12][C:13]([OH:15])=[O:14])([C:9]([OH:11])=[O:10])[OH:8].[Cl:18][C:19]1[CH:20]=[C:21]([C@H:26]([CH2:44][CH2:45][N:46]2[CH2:51][CH2:50][CH:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[NH:58]S(C)(=O)=O)[CH2:48][CH2:47]2)[CH2:27][N:28]([CH3:43])[C:29]([C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=[C:33]([C:41]#[N:42])[CH:32]=2)=[O:30])[CH:22]=[CH:23][C:24]=1[Cl:25].C(N(CC)CC)C>C(Cl)Cl.CCOCC>[C:5]([OH:17])(=[O:16])[CH2:6][C:7]([CH2:12][C:13]([OH:15])=[O:14])([C:9]([OH:11])=[O:10])[OH:8].[Cl:18][C:19]1[CH:20]=[C:21]([C@H:26]([CH2:44][CH2:45][N:46]2[CH2:51][CH2:50][CH:49]([C:52]3[CH:57]=[CH:56][CH:55]=[CH:54][C:53]=3[NH:58][C:1](=[O:3])[CH3:2])[CH2:48][CH2:47]2)[CH2:27][N:28]([CH3:43])[C:29]([C:31]2[C:40]3[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:34]=[C:33]([C:41]#[N:42])[CH:32]=2)=[O:30])[CH:22]=[CH:23][C:24]=1[Cl:25]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 18715623HCID 18715623, compound

Product 1

HCID 18715614HCID 18715614, compoundYield 104.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

Acetyl chloride (0.060 g) was added to a solution of 4-(2-aminophenyl)-N-Boc-piperidine (0.070 g) (Example 21 sub-part (b)) and triethylamine (0.090 g) in DCM (2 mL) and stirred overnight. The reaction was diluted with Et2O and extracted sequentially with aqueous sodium bicarbonate and 1N HCl. The organic extract was dried and evaporated to give the title compound (0.070 g) as a colorless oil. MS m/z 341 (M+Na). 1H NMR (CDCl3) δ 7.26 (m, 4H), 7.69 (br, 1H), 4.15 (m, 2H), 2.67 (m, 3H), 2.23 (s, 3H), 1.75 (m, 4H), 1.48 (s, 9H).

Workup

  1. extractionextracted sequentially with aqueous sodium bicarbonate and 1N HCl
  2. extractionThe organic extract
  3. customwas dried
  4. customevaporated

Sources & evidence

ORD record
ord-582798f887504fc68e5d5f4fd4634ec8
Source dataset
uspto-grants-2002_04
Patent number
US06365602B1

Reaction notes

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