Triethylamine → HCID 21708984, compound

HRID 651872Notes

Reaction equation

HRID 651872 reaction equation
[CH2:1]([O:8][C:9]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:12]2[N:13]([CH2:22][OH:23])[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([O:20][CH3:21])=[O:19])[C:11]=2[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.[CH3:37][S:38](Cl)(=[O:40])=[O:39]>CCOC(C)=O.CCCCCC>[CH2:1]([O:8][C:9]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:12]2[N:13]([CH2:22][O:23][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:14][CH2:15][CH2:16][CH:17]([C:18]([O:20][CH3:21])=[O:19])[C:11]=2[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 21709011HCID 21709011, compound

Product 1

HCID 21708984HCID 21708984, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Following the general procedure detailed for 84, 91 (0.029 g, 0.074 mmol, 1 equiv) was treated with Et3N (0.052 mL, 0.371 mmol, 5 equiv) and CH3SO2Cl (0.017 mL, 0.148 mmol, 2 equiv). Radial chromatography (SiO2, 1 mm plate, 50% EtOAc-hexane) furnished 93 (0.032 g, 0.035 g theoretical, 91%) as a white solid: mp 130-132° C.; 1H NMR (500 MHz, CDCl3) major rotamer δ 8.40 (d, J=8.5 Hz, 1H), 8.13 (d, J=8.5 Hz, 1H), 7.61-7.35 (m, 7H), 6.63 (s, 1H), 5.27-5.17 (m, 2H), 4.51-4.33 (m, 4H), 3.60 (s, 3H), 2.86-2.81 (m, 1H), 2.54 (s, 3H), 2.32-2.23 (m, 1H), 2.07-2.04 (m, 1H), 1.76-1.70 (m, 2H); 13C NMR (125 MHz, CDCl3) major rotamer δ 155.3, 153.7, 139.5, 136.6, 133.1, 128.6 (2C), 128.0 (2C), 127.7, 127.6, 127.3, 125.4, 124.3, 123.4, 122.8, 106.9, 71.1, 70.1, 53.0, 48.3, 36.8, 36.2, 26.7, 24.5; IR (film) νmax 3063, 3022, 2938, 2858, 1701, 1593 cm−1; FABHRMS (NBA) m/z 470.1648 (M+H+, C25H27NO6S requires 470.1637).

Sources & evidence

ORD record
ord-d23b71d030a0493ca1afc7ea6a55a16c
Source dataset
uspto-grants-2001_08
Patent number
US06281354B1

Reaction notes

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