Triethylamine → HCID 53781083, compound

HRID 236510Notes

Reaction equation

HRID 236510 reaction equation
[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([OH:23])=O)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:39][C@H:40]([C:44]([NH:46][C@H:47]([C:51]([OH:53])=[O:52])[C@@H:48]([CH3:50])[OH:49])=[O:45])[C@@H:41]([CH3:43])[OH:42].C(N(CC)CC)C>O.O1CCCC1>[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([NH:39][C@H:40]([C:44]([NH:46][C@H:47]([C:51]([OH:53])=[O:52])[C@@H:48]([CH3:50])[OH:49])=[O:45])[C@@H:41]([CH3:43])[OH:42])=[O:23])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11321969Thr-ThrHCID 134890283-Hexadecanoyloxyoctadecanoic acid

Product 1

HCID 53781083HCID 53781083, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

A solution of N-hydroxysuccinimide ester of 3-hexadecanoyloxyoctadecanoic acid (1.5 g) prepared by the method of Example 8 (1), L-threonyl-L-threonine (0.7 g) and triethylamine (0.44 ml) in tetrahydrofuran water (100 ml-200 ml) was stirred at room temperature for 5 hours. After removal of tetrahydrofuran under reduced pressure, the residue was acidified with 1% hydrochloric acid (100 ml) and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and concentrated to give a residue which was purified by column chromatography on silica gel. Elution with a mixture of chloroform and methanol (20:1) afforded N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-threonine (1.2 ) as powder.

Workup

  1. customAfter removal of tetrahydrofuran under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified by column chromatography on silica gel
  8. washElution
  9. additionwith a mixture of chloroform and methanol (20:1)

Sources & evidence

ORD record
ord-925ef52d215f43d9bbf8b983ae67a2a7
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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