1-Tetradecanol → HCID 23255086, compound

HRID 429747Notes

Reaction equation

HRID 429747 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([OH:15])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:16](O)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1CCC(N=C=NC2CCCCC2)CC1>C(OCC)(=O)C>[CH2:29]([O:14][C:13](=[O:15])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH3:16]

Participants

5

Reactant 3

HCID 82091-TetradecanolHCID 10868DicyclohexylcarbodiimideHCID 14349Benzyloxycarbonylglycine

Product 1

HCID 23255086HCID 23255086, compoundYield 59.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-benzyloxycarbonyl glycine (3 g, 14.3 mmol), tetradecylalcohol (3.07 g, 14.3 mmol) an N,N-dimethylaminopyridine (87 mg, 10.3 mmol) in ethyl acetate (100 ml) was added DCC (2.98 g, 2.34 mmol) and the resulting mixture was stirred for 2 h at room temperature. After the precipitation which appeared was filtered off, the filtrate was concentrated in vacuo. The residue was washed with ethanol to give N-benzyloxycarbonylglycine tetradecyl ester (7) (3.46 g, 59.5%) as crystal.

Workup

  1. customAfter the precipitation which
  2. filtrationappeared was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. washThe residue was washed with ethanol

Sources & evidence

ORD record
ord-3a195cd4a3cf4af096cae678a012387a
Source dataset
uspto-grants-2001_11
Patent number
US06319902B1

Reaction notes

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