Acetyl chloride → HCID 86607898, compound

HRID 736799Notes

Reaction equation

HRID 736799 reaction equation
[C:1]([O:5][NH:6][C:7]([C@:9]1([CH3:38])[C@H:14]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:21][CH:20]=2)(=[O:18])=[O:17])[CH2:13][CH2:12][NH:11][CH2:10]1)=[O:8])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:46](Cl)(=[O:48])[CH3:47]>C(Cl)Cl.C(OCC)(=O)C>[C:46]([N:11]1[CH2:12][CH2:13][C@@H:14]([NH:15][S:16]([C:19]2[CH:20]=[CH:21][C:22]([O:25][CH2:26][C:27]3[C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=[C:29]([CH3:37])[CH:28]=3)=[CH:23][CH:24]=2)(=[O:18])=[O:17])[C@@:9]([CH3:38])([C:7]([NH:6][O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:8])[CH2:10]1)(=[O:48])[CH3:47]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 86607899HCID 86607899, compound

Product 1

HCID 86607898HCID 86607898, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

(3S,4R)-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (323 mg, 0.597 mmol) was dissolved in CH2Cl2 (5 mL). The solution was cooled to 0° C., then triethylamine (100 μL) and acetylchloride (50 μL) were added. The reaction was stirred for 1 h, then diluted with ethyl acetate and washed with saturated aqueous Na2CO3 (2×) and brine (2×). The organic layer was isolated, dried over Na2SO4, concentrated, and then purified via column chromatography on silica gel eluting with 5% MeOH/CH2Cl2 to give (3S,4R)-1-acetyl-N-tert-butoxy-3-methyl-4-(4-((2-methylquinolin-4-yl)methoxy)phenylsulfonamido)piperidine-3-carboxamide (341 mg, 0.585 mmol, quant) as a colorless solid. 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.09 (s, 3H) 1.22-1.28 (m, 9H) 1.55 (qd, J=12.93, 4.67 Hz, 1H) 1.88 (ddd, J=13.52, 2.78, 2.65 Hz, 1H) 2.07-2.10 (m, 3H) 2.33-2.39 (m, 1H) 2.75 (s, 3H) 3.09-3.18 (m, 1H) 3.24 (ddd, J=12.19, 8.53, 3.79 Hz, 1H) 3.78 (dt, J=13.58, 2.18 Hz, 1H) 4.76 (dd, J=14.91, 2.53 Hz, 1H) 5.55 (s, 2H) 7.08-7.14 (m, 2H) 7.42 (s, 1H) 7.53-7.58 (m, 1H) 7.70-7.75 (m, 1H) 7.83-7.87 (m, 2H) 7.89-7.93 (m, 1H) 8.07-8.11 (m, 1H) 9.93 (s, 1H).

Workup

  1. washwashed with saturated aqueous Na2CO3 (2×) and brine (2×)
  2. customThe organic layer was isolated
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. custompurified via column chromatography on silica gel eluting with 5% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-529f065a50ee41748a1501278312a4b8
Source dataset
uspto-grants-2009_09
Patent number
US07595327B2

Reaction notes

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