Triethylamine → HCID 72594823, compound

HRID 1168194Notes

Reaction equation

HRID 1168194 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:4][C:3]=1[C:15](=[O:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18].C(N(CC)CC)C.C1(C)C(S([N:39]=[N+:40]=[N-])(=O)=O)=CC=CC=1>CC#N>[N+:39](=[C:16]([C:15]([C:3]1[CH:4]=[C:5]([CH2:8][N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)[CH:6]=[CH:7][C:2]=1[F:1])=[O:22])[C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N-:40]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12971970HCID 12971970, compoundHCID 217089242-Methylbenzene-1-sulfonyl azide

Product 1

HCID 72594823HCID 72594823, compoundYield 86.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3-(2-fluoro-5-(4-morpholinylmethyl)phenyl)-3-oxopropanoate (Preparation 9, 5.00 g) and triethylamine (2.48 mL) in 50 mL CH3CN cooled to 0° C. is added toluenesulfonyl azide (3.51 g, prepared according to Org. Prep. Proc. Intl., 1981, 13, 112) in 10 mL CH3CN. The reaction is stirred at 0° C. for 15 min then at room temperature for 2 h. The reaction is concentrated (below 50° C.). 2N NaOH (25 mL) is added. The aqueous layer is extracted with CHCl3 (3×). The combined organic layers are washed, dried and concentrated to yield 4.68 g (86%) of the desired product as a yellow oil. Physical characteristics are as follows: 1H NMR (CDCl3) δ7.52, 7.44, 7.06, 4.24, 3.75, 3.55, 2.50, 1.24; MS (ESI+) for C16H18FN3O4 m/z 336.1 (M+H)+.

Workup

  1. waitat room temperature for 2 h
  2. concentrationThe reaction is concentrated (below 50° C.)
  3. addition2N NaOH (25 mL) is added
  4. extractionThe aqueous layer is extracted with CHCl3 (3×)
  5. washThe combined organic layers are washed
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-18d00e44a9aa434fb5fb533233fee5fd
Source dataset
uspto-grants-2003_09
Patent number
US06624160B2

Reaction notes

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