N-(3-hydroxypropyl)glycine benzyl ester → N-(3-hydroxypropyl)-N-[(R)-3-decanoyloxytetradecanoyl]glycine benzyl ester

HRID 381191Notes

Reaction equation

HRID 381191 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[CH2:10][NH:11][CH2:12][CH2:13][CH2:14][OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:17]([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]([OH:33])=O)(=[O:27])[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(Cl)CCl.CI>C(Cl)Cl>[CH2:1]([O:8][C:9](=[O:16])[CH2:10][N:11]([CH2:12][CH2:13][CH2:14][OH:15])[C:31](=[O:33])[CH2:30][C@H:29]([O:28][C:17](=[O:27])[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])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 9991156N-(3-hydroxypropyl)glycine benzyl esterHCID 10810916(R)-3-decanoyloxytetradecanoic acidHCID 86585083Edc-methiodide

Product 1

HCID 54371661N-(3-hydroxypropyl)-N-[(R)-3-decanoyloxytetradecanoyl]glycine benzyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the same manner as described in Example 2-(5), N-(3-hydroxypropyl)glycine benzyl ester (450 mg, 2.0 mmol) was acylated with (R)-3-decanoyloxytetradecanoic acid (1.0 g, 2.5 mmol) in the presence of EDC·MeI (900 mg, 3.0 mmol) in CH2Cl2 to afford 0.76 g (63%) of N-(3-hydroxypropyl)-N-[(R)-3-decanoyloxytetradecanoyl]glycine benzyl ester as a colorless oil: 1H NMR (CDCl3) (1:1 mixture of rotomers) δ 0.88 (t, 6H, J=6.6 Hz), 1.1-1.7 (m, 35H), 1.78 (m, 1H), 2.26 (q, 2H, J=7.6 Hz), 2.37 and 2.54 (2 dd, 1H, J=14.9, 6.9 Hz), 2.60 and 2.89 (2 dd, 1H, J=14.8, 6.0 Hz), 3.51 (m, 4H), 3.70 (m, 1H), 3.95-4.25 (m, 2H), 5.1-5.25 (m, 3H),7.35(m, 5H).

Sources & evidence

ORD record
ord-da170f258c084db39633d4a7ba8f1269
Source dataset
uspto-grants-2001_10
Patent number
US06303347B1

Reaction notes

Loading…