Triethylamine → N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serinamide

HRID 277598Notes

Reaction equation

HRID 277598 reaction equation
Cl.[NH2:2][C@H:3]([C:6]([NH2:8])=[O:7])[CH2:4][OH:5].[C:9]([O:24][C@H:25]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:26][C:27](O)=[O:28])(=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].C(N(CC)CC)C.CCOC1N(C(OCC)=O)C2C(=CC=CC=2)C=C1>C(Cl)Cl>[C:9]([O:24][C@H:25]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[CH2:26][C:27]([NH:8][C:6](=[O:7])[C@H:3]([CH2:4][OH:5])[NH2:2])=[O:28])(=[O:23])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 278332-Ethoxy-1-(ethoxycarbonyl)-1,2-dihydroquinolineHCID 11048724(R)-3-tetradecanoyloxytetradecanoic acidHCID 16212403L-Serinamide hydrochloride

Product 1

HCID 86585084N-[(R)-3-tetradecanoyloxytetradecanoyl]-L-serinamideYield 71.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of L-serinamide hydrochloride (0.157 g, 1.18 mmol) and (R)-3-tetradecanoyloxytetradecanoic acid (0.61 g, 1.34 mmol) in CH2Cl2 (6 mL) was treated with triethylamine (0.18 mL, 1.3 mmol) and the resulting solution was stirred with 4 Å molecular sieves for 30 min. EEDQ (0.437 g, 1.77 mmol) was then added and the mixture was stirred for 16 h at room temperature. The product that precipitated was collected and washed with CH2Cl2 (2×25 mL) to give 0.455 g (71%) of N-[(R)-3-tetradecanoyloxytetradecanoyl]-L -serinamide as a colorless powder: mp 126-130° C.; 1H NMR (CDCl3) δ 0.88 (t, 6H, J=˜7 Hz), 1.15-1.7 (m, 42 H), 2.31 (t, 2 H, J=7.5 Hz), 2.51 (d, 2 H, J=6.3 Hz), 3.56 (br s, 1 H), 3.65 (dd, 1 H, J=1 1.2, 5.5 Hz), 3.86 (dd, 1 H, J=1 1.2, 4.5 Hz), 4.21 (s, 2 H), 4.40 (m, 1 H), 5.22 (m, 1 H).

Workup

  1. stirringthe mixture was stirred for 16 h at room temperature
  2. customThe product that precipitated
  3. customwas collected
  4. washwashed with CH2Cl2 (2×25 mL)

Sources & evidence

ORD record
ord-44744ccee4864f66b8b36f238d807613
Source dataset
uspto-grants-2002_03
Patent number
US06355257B1

Reaction notes

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