Triethylamine → HCID 69948043, compound

HRID 2394033Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:20])[CH3:19])=[CH:14][CH:13]=1.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.C(N(CC)CC)C.[C:41]1([CH2:47][CH2:48][S:49][CH:50]([C:54](O)=[O:55])[C:51](O)=[O:52])[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1.[K+].[Br-]>>[CH3:1][O:2][C:3](=[O:21])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[O:20][C:51](=[O:52])[C:50]([S:49][CH2:48][CH2:47][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)=[C:54]([OH:55])[CH:19]=2)=[CH:16][CH:17]=1

Participants

Reactant 5

HCID 8471Triethylamine

HCID 65367Trimethylsilyl triflate

HCID 253877Potassium Bromide

HCID 19596072[(Phenylethyl)thio]propanedioic acid

HCID 69948036HCID 69948036, compound

Product 1

HCID 69948043HCID 69948043, compound

Procedure

The title compound was prepared by Method A using 2-[[(4-acetyl)phenoxy]methyl]benzoic acid methyl ester (2.0 g, 7.04 mmol), trimethylsilyltrifluoromethylsulfonate (1.57 g, 7.04 mmol), triethylamine (1.42 g, 14.08 mmol) and diethyl ester of [(2-phenylethyl)thio]propanedioic acid (1.04 g, 3.52 mmol). m.p. 161°-162° C.; 1H NMR (400 MHz, DMSO-d6) δ 2.78 (t, 2 H), 2.97 (t, 2 H), 3.81 (s, 3 H), 5.5 (s, 2 H), 6.69 (s, 1 H), 7.14 (m, 3 H), 7.25 (m, 4 H), 7.5 (m, 2 H), 7.78 (m, 2 H), 7.78 (d, 2 H), 7.94 (d, 1 H); IR (KBr) 3028, 2949, 2909, 2675, 1715, 1638, 1510, 1402, 1291, 1267, 1181, 1030, 828, 747 cm-1 ; MS (CI) m/e 489 (M+H, 51), 384 (3), 353 (1), 149 (100), 135 (47), 105 (33).

Sources & evidence

ORD record: ord-4e094da846694a3b9fe526a22af3664c
Source dataset: uspto-grants-1998_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05808062

Reaction notes

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