1,2-Dichloroethane → 3-benzyloxy-(R)-2-[(R)-3-tetradecanoyloxytetradecanoylamino]propanol

HRID 277592Notes

Reaction equation

HRID 277592 reaction equation
[NH2:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].[C:14]([O:29][C@H:30]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:31][C:32](O)=[O:33])(=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27].C(Cl)CCl.CI>C(Cl)Cl>[CH2:7]([O:6][CH2:5][C@H:2]([NH:1][C:32](=[O:33])[CH2:31][C@H:30]([O:29][C:14](=[O:28])[CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:3][OH:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6328Methyl iodideHCID 11048724(R)-3-tetradecanoyloxytetradecanoic acidHCID 141184082-Amino-3-(benzyloxy)propan-1-ol

Product 1

HCID 541503963-benzyloxy-(R)-2-[(R)-3-tetradecanoyloxytetradecanoylamino]propanolYield 76.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of (R)-2-amino-3-benzyloxy-1-propanol (0.46 g, 2.33 mmol) and (R)-3-tetradecanoyloxytetradecanoic acid (1.29 g, 2.83 mmol) in CH2Cl2 (20 mL) was treated with EDC.MeI (0.78 g, 2.79 mmol) and stirred for 16 h at room temperature. The reaction mixture was filtered through a short pad of Celite® and concentrated. Flash chromatography on silica gel with 45% EtOAc-hexanes afforded 1.1 g (69%) of 3-benzyloxy-(R)-2-[(R)-3-tetradecanoyloxytetradecanoylamino]propanol as a colorless solid: mp 42-44.5° C.; 1H NMR δ 0.88 (t, 6 H, J=˜6.5 Hz), 1.0-1.7 (m, 42 H), 2.50 (t, 2 H, J=7.5 Hz), 2.46 (m, 2 H), 3.56 (br s, 1 H), 3.5-3.75 (m, 3 H), 3.78 (dd, 1 H, J=11, 4 Hz), 4.08 (m, 1 H), 4.51 (s, 2 H), 5.17 (m, 1 H), 6.36 (d, 1 H, J=7.8 Hz), 7.2-7.4 (m, 5 H).

Workup

  1. filtrationThe reaction mixture was filtered through a short pad of Celite®
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-4b9cacf35a9845cc9e65ee8d39a336cd
Source dataset
uspto-grants-2002_03
Patent number
US06355257B1

Reaction notes

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