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

HRID 381180Notes

Reaction equation

HRID 381180 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]CCC.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][CH3:21])[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 854069(S)-Benzyl 2-amino-3-hydroxypropanoateHCID 10810916(R)-3-decanoyloxytetradecanoic acidHCID 86585083Edc-methiodide

Product 1

HCID 53870673N-[(R)-3-heptanoyloxytetradecanoyl]-L-serine benzyl esterYield 90.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In the same manner as described in Example 2-(5), L-serine benzyl ester (250 mg, 1.08 mmol) was acylated with (R)-3-decanoyloxytetradecanoic acid (478 mg, 1.2 mmol) in the presence of EDC·MeI (357 mg, 1.2 mmol) in CH2Cl2 to afford 0.52 g (84%) of N-[(R)-3-heptanoyloxytetradecanoyl]-L-serine benzyl ester: mp 52-53° C.; 1H NMR (CDCl3) δ 0.87 (t, 6H, J=6.9 Hz), 1.1-1.7 (m, 34H), 2.29 (t, 2 H, J=7.5 Hz), 2.49 (d, 2H, J=5.8 Hz), 3.67 (s, 1H), 3.97 (m, 2H), 4.63 (m, 1H), 5.19 (m, 3H), 6.61 (d, 1H, J=7.1 Hz), 7.35 (brs, 5H).

Sources & evidence

ORD record
ord-fe4046a9b01743f58f584a0af1ce1b2d
Source dataset
uspto-grants-2001_10
Patent number
US06303347B1

Reaction notes

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