Triethylamine → HCID 20767772, compound

HRID 1825121Notes

Reaction equation

HRID 1825121 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([OH:13])=O)[S:10][C:3]=12.[Li].Cl.[CH3:16][O:17][C:18](=[O:23])[C@H:19]([CH2:21][OH:22])[NH2:20].CCN(CC)CC>O=S(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[CH:8]=[C:9]([C:11]([NH:20][C@H:19]([C:18]([O:17][CH3:16])=[O:23])[CH2:21][OH:22])=[O:13])[S:10][C:3]=12

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723730L-Serine, methyl ester, hydrochloride (1:1)HCID 66619470HCID 66619470, compound

Product 1

HCID 20767772HCID 20767772, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 24386Thionyl ChlorideSolvent

Procedure

This material was prepared from lithium 7-chlorothieno[3,2-b]pyridine-2-carboxylic acid (2.69 g, 12.25 mmole), SOCl2 (10 ml), L-serine methyl ester hydrochloride (2.86 g, 18.4 mmole) and Et3N (5.12 ml, 37.7 mmole) in a manner as previously described for example 9d to give a white solid (2.09 g, 54%). 1H NMR (300 MHz, CDCl3) δ 8.61 (1H, d, J=5.1 Hz), 8.02 (1H, s), 7.35 (1H, d, J=5.1 Hz), 4.89 (1H, m), 4.15 (2H, m), 3.84 (3H, m).

Sources & evidence

ORD record
ord-50ab2489fa0c4ec7a97a21e0812d2eca
Source dataset
uspto-grants-2006_05
Patent number
US07045528B2

Reaction notes

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