(S)-Benzyl 2-amino-3-hydroxypropanoate → N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serine benzyl ester

HRID 381176Notes

Reaction equation

HRID 381176 reaction equation
[CH2:1]([O:8][C:9](=[O:14])[C@H:10]([CH2:12][OH:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:15]([O:30][C@H:31]([CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[CH2:32][C:33](O)=[O:34])(=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28].C(Cl)CCl.CI>>[CH2:1]([O:8][C:9](=[O:14])[C@H:10]([CH2:12][OH:13])[NH:11][C:33](=[O:34])[CH2:32][C@H:31]([O:30][C:15](=[O:29])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH3:46])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 854069(S)-Benzyl 2-amino-3-hydroxypropanoateHCID 11048724(R)-3-tetradecanoyloxytetradecanoic acidHCID 86585083Edc-methiodide

Product 1

HCID 54189790N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serine benzyl esterYield 94.1%

Procedure

In the same manner as described in Example 2-(5), L-serine benzyl ester (0.212 g, 1.08 mmol) was acylated with (R)-3-tetradecanoyloxytetradecanoic acid (0.541 g, 1.19 mmol) in the presence of EDC·MeI (0.353 g, 1.19 mmol) to give 0.642 g (94%) of N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serine benzyl ester as a waxy solid: mp 56-61° C.; 1H NMR (CDCl3) δ 0.88 (t, 6H, J=7 Hz), 1.1-1.7 (m, 42H), 2.29 (t, 2H, J=7.5 Hz), 2.50 (m, 2H), 3.87 (br t, 1H), 3.95 (m, 2H), 4.65 (m, 1H), 5.1-5.25 (m, 3H), 6.69 (d, 1H, J=7 Hz), 7.34 (br s, 5H).

Sources & evidence

ORD record
ord-5a3a6203fb7a4b94a2aad2d4e85eaf18
Source dataset
uspto-grants-2001_10
Patent number
US06303347B1

Reaction notes

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