Triethylamine → HCID 57234797, compound

HRID 1872446Notes

Reaction equation

HRID 1872446 reaction equation
[NH2:1][C@H:2]([C@H:4]([OH:20])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH3:3].[C:21](N1C=CN=C1)(N1C=CN=C1)=[O:22].C(N(CC)CC)C>ClCCl>[CH3:3][C@H:2]1[C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[O:20][C:21](=[O:22])[NH:1]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 9925886Spisulosine

Product 1

HCID 57234797HCID 57234797, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(2S, 3R)-2-amino-3-octadecanol (155, 750 μg, 2.6 μmol) was dissolved in dichloromethane (100 μL) to which 1,1'-carbonyldiimidazole (0.85 mg, 5.3 μmol) and triethylamine (0.4 μL, 2.9 μmol) was added. The solution was stirred for 5 h and then the solvent removed by a stream of nitrogen. The crude product 158 was analyzed without purification: IR (NaCI) 36, 2919, 2851, 1742, 1713, 1551, 1470, 1395, 1321, 49, 1239, 1094, 1061, 1001, 768, 743, 664 cm-1 ; FABMS m/z 785, 623, 474, 406, 362, 328, 312, 286, 268.

Workup

  1. additionwas added
  2. customthe solvent removed by a stream of nitrogen
  3. customThe crude product 158 was analyzed without purification

Sources & evidence

ORD record
ord-85bb1d481973452baea9b96d477866ec
Source dataset
uspto-grants-2000_08
Patent number
US06107520

Reaction notes

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