(R)-3-tetradecanoyloxytetradecanoic acid → HCID 54438210, compound

HRID 381190Notes

Reaction equation

HRID 381190 reaction equation
[C:1]([O:5][C:6](=[O:12])[CH2:7][NH:8][CH2:9][CH2:10][OH:11])([CH3:4])([CH3:3])[CH3:2].[C:13]([O:28][C@H:29]([CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])[CH2:30][C:31](O)=[O:32])(=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(Cl)CCl.CI>>[C:1]([O:5][C:6](=[O:12])[CH2:7][N:8]([CH2:9][CH2:10][OH:11])[C:31](=[O:32])[CH2:30][C@H:29]([O:28][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 11048724(R)-3-tetradecanoyloxytetradecanoic acidHCID 11062917Tert-butyl 2-[(2-hydroxyethyl)amino]acetateHCID 86585083Edc-methiodide

Product 1

HCID 54438210HCID 54438210, compoundYield 52.6%

Procedure

In the same manner as described in Example 2-(5), N-(2-hydroxyethyl)glycine t-butyl ester (0.25 g, 1.43 mmol) was acylated with (R)-3-tetradecanoyloxytetradecanoic acid (0.714 g, 1.57 mmol) in the presence of EDC·MeI (0.466 g, 1.57 mmol) to give 0.46 g (51%) of N-(2-hydroxyethyl)-N-[(R)-3-tetradecanoyloxytetradecanoyl]glycine t-butyl ester as an amorphous solid: 1H NMR (CDCl3) δ 0.88 (t, 6H, J=6.5 Hz), 1.15-1.7 (m, 51H), 2.26 (t, 2H, J=7.5 Hz), 2.60 (dd, 1H, J=6.5, 15 Hz), 2.86 (dd, 1H, J=6.7, 15 Hz), 3.40-4.15 (m, 7H), 5.25 (m, 1H).

Sources & evidence

ORD record
ord-c81defc25a3e45a28016287b08934f3b
Source dataset
uspto-grants-2001_10
Patent number
US06303347B1

Reaction notes

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