2-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinoline → N-[(R)-3-decanoyloxytetradecanoyl]-L-serinamide

HRID 381189Notes

Reaction equation

HRID 381189 reaction equation
Cl.[NH2:2][C@H:3]([C:6]([NH2:8])=[O:7])[CH2:4][OH:5].[C:9]([O:20][C@H:21]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:22][C:23](O)=[O:24])(=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18].CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>C(Cl)Cl>[C:9]([O:20][C@H:21]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH3:36])[CH2:22][C:23]([NH:8][C:6](=[O:7])[C@H:3]([CH2:4][OH:5])[NH2:2])=[O:24])(=[O:19])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 10810916(R)-3-decanoyloxytetradecanoic acidHCID 16212403L-Serinamide hydrochloride

Product 1

HCID 86585085N-[(R)-3-decanoyloxytetradecanoyl]-L-serinamideYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the same manner as described in Example 25-(1), L-serinamide hydrochloride (169 mg, 1.2 mmol) was acylated with (R)-3-decanoyloxytetradecanoic acid (478 mg, 1.2 mmol) in the presence of EEDQ (371 mg, 1.5 mmol) in CH2Cl2 to afford 428 mg (74%) of N-[(R)-3-decanoyloxytetradecanoyl]-L-serinamide as a white solid: 1H NMR (CDCl3) δ 0.88 (t, 6H), 1.1-1.7 (m, 34H), 2.33 (t, 2H, J=7.5 Hz), 2.54 (d, 2H, J=6.6 Hz), 3.35 (s, 2H), 3.72 (dd, 1H, J=11.0, 5.2 Hz), 3.84 (dd, 11H, J=11.3, 5.0 Hz), 4.20 (t, 1H, J=5.1 Hz), 5.26 (t, 1H, J=6.4 Hz).

Sources & evidence

ORD record
ord-8cc4974613774522be7d2657f27729c8
Source dataset
uspto-grants-2001_10
Patent number
US06303347B1

Reaction notes

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