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

HRID 1884778
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HRID 1884778 반응식
[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:27][C@H:28]([CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:29][C:30](O)=[O:31])(=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25].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:30](=[O:31])[CH2:29][C@H:28]([O:27][C:15](=[O:26])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
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참가 물질

5

반응물 3

HCID 854069(S)-Benzyl 2-amino-3-hydroxypropanoateHCID 54121365(R)-3-undecanoyloxytetradecanoic acidHCID 86585083Edc-methiodide

생성물 1

HCID 54138306N-[(R)-3-undecanoyloxytetradecanoyl]-L-serine benzyl ester수율 92%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In the same manner as described in Example 2-(5), L-serine benzyl ester (390 mg, 2.0 mmol) as acylated with (R)-3-undecanoyloxytetradecanoic acid (905 mg, 2.2 mmol) in the presence of EDC MeI (745 mg, 2.5 mmol) in CH2Cl2 to afford 1.08 g (92%) of N-[(R)-3-undecanoyloxytetradecanoyl]-L-serine benzyl ester: mp 53-54° C.: 1H NMR (CDCl3) δ 0.88 (t, 6 H, J=6.9 Hz), 1.1-1.7 (m, 44 H), 2.30 (t, 2 H, J=7.7 Hz), 2.49 (d, 2 H, J=5.8 Hz), 3.99 (m, 2 H), 4.65 (m, 1 H), 5.19 (m, 3 H), 6.58 (d, 1 H, J=6.9 Hz), 7.35 (br s, 5 H).

출처 및 근거

ORD 기록
ord-2aa6fe0684fc412ba6f4ddc91c887974
출처 데이터셋
uspto-grants-2004_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06764840B2

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