benzyl (2R)-2-amino-3-hydroxypropanoate → N-[(R)-3-decanoyloxytetradecanoyl]-D-serine benzyl ester

HRID 1983949Notes

Reaction equation

HRID 1983949 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:26][C@H:27]([CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[CH2:28][C:29](O)=[O:30])(=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].C(Cl)CCl.CI>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:14])[C@@H:10]([CH2:12][OH:13])[NH:11][C:29](=[O:30])[CH2:28][C@H:27]([O:26][C:15](=[O:25])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 854068benzyl (2R)-2-amino-3-hydroxypropanoateHCID 10810916(R)-3-decanoyloxytetradecanoic acidHCID 86585083Edc-methiodide

Product 1

HCID 54524589N-[(R)-3-decanoyloxytetradecanoyl]-D-serine benzyl esterYield 91.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the same manner as described in Example 2-(5), D-serine benzyl ester (390 mg, 2.0 mmol) was acylated with (R)-3-decanoyloxytetradecanoic acid (875 mg, 2.2 mmol) in the presence of EDC·MeI (745 mg, 2.5 mmol) in CH2Cl2 to afford 1.05 g (91%) of N-[(R)-3-decanoyloxytetradecanoyl]-D-serine benzyl ester: mp 51-52° C.; 1H NMR (CDCl3) δ 0.88 (m, 6H), 1.1-1.7 (m, 34H), 2.30 (t, 2H, J=7.7 Hz), 2.50 (m, 2H),3.68 (s, 1H), 3.93 (d, 2H, J=3.1 Hz), 4.62 (m, 1H), 5.22 (m, 3H), 6.63 (d, 1H, J=6.9 Hz), 7.35 (br s, 5H).

Sources & evidence

ORD record
ord-b698d127d40c4d21bdb0dae22dd96516
Source dataset
uspto-grants-2009_06
Patent number
US07541020B2

Reaction notes

Loading…