Acetyl chloride → HCID 57841373, compound

HRID 733534Notes

Reaction equation

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

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 11191550HCID 11191550, compound

Product 1

HCID 57841373HCID 57841373, compound

Procedure

The title compound was prepared following the procedure G using the hydrochloride salt of methyl 5-{[(4-dec-1-ynylbenzyl)amino]methyl}-2-(2-methoxy-2-oxoethoxy)benzoate and acetyl chloride (purification by flash chromatography on SiO2, chloroform/MeOH 99:1 to 90:10) as a colorless oil (72%). M+ (ESI): 521.9. HPLC, Rt: 5.4 min (purity: 100%). 1H NMR (CDCl3) δ: 7.62 (m, 1H), 7.41-7.05 (m, 5H), 6.85 (m, 1H), 4.75 (s, 1H), 4.73 (s, 1H), 4.55 (s, 1H), 4.53 (s, 1H), 4.41 (s, 1H), 4.38 (s, 1H), 3.92 (s, 1.5H), 3.90 (s, 1.5H), 3.82 (s, 1.5H), 3.81 (s, 1.5H), 2.41 (m, 2H), 2.21 (s, 1.5H), 2.20 (s, 1.5H), 1.62 (m, 2H), 1.45 (m, 2H), 1.31 (brs, 8H), 0.90 (t, J=6.6 Hz, 3H).

Sources & evidence

ORD record: ord-4b43ecb6723b47b5bfa3de373268c981
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589232B2

Reaction notes

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