4-Methylmorpholine → HCID 21709352, compound

HRID 651742Notes

Reaction equation

HRID 651742 reaction equation
C(O[C:6]([NH:8][CH2:9][CH2:10][N:11]([CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][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])=O)(C)(C)C.C[N:49]1[CH2:54][CH2:53]OCC1.C(OC([NH:62][CH2:63][CH2:64][CH2:65]Br)=O)(C)(C)C>FC(F)(F)C(O)=O.C(Cl)Cl>[NH2:62][CH2:63][CH2:64][CH2:65][N:8]([CH2:6][CH2:53][CH2:54][NH2:49])[CH2:9][CH2:10][N:11]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][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])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47]

Participants

6

Reactant 3

HCID 79724-MethylmorpholineHCID 4460490tert-butyl N-(3-bromopropyl)carbamateHCID 15408296HCID 15408296, compound

Product 1

HCID 21709352HCID 21709352, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

200 mg (0.3 mmol, MW 665.12) of N-tert-butoxycarbonyl-N′,N′-dioctadecylethylenediamine are dissolved in 2 ml of a mixture of trifluoroacetic acid and methylene chloride (1:3 v/v). After two hours, the mixture is subject to rotary evaporation and dried for 2 hours under a high vacuum. The residue is then taken up in 20 ml of chloroform, and 1 ml (920 mg, 4.5 mmol, MW 101.15, d=0.92) of 4-methylmorpholine is added. 640 mg (2.68 mmol, MW 238.13) of N-(tert-butoxycarbonyl)-3-bromopropylamine are then added. After boiling for 48 hours under reflux, the whole is concentrated by rotation and the BOC-protected precursor product is purified by flash chromatography. The product is then dissolved in 2 ml of a mixture of trifluoroacetic acid and methylene chloride (1:3 v/v), concentrated by rotary evaporation and lyophilised.

Workup

  1. customthe mixture is subject to rotary evaporation
  2. customdried for 2 hours under a high vacuum
  3. waitAfter boiling for 48 hours
  4. temperatureunder reflux
  5. concentrationthe whole is concentrated by rotation
  6. customthe BOC-protected precursor product is purified by flash chromatography
  7. dissolutionThe product is then dissolved in 2 ml of a mixture of trifluoroacetic acid and methylene chloride (1:3 v/v)
  8. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-e177d2532f18484d829a839141be76f6
Source dataset
uspto-grants-2001_08
Patent number
US06281371B1

Reaction notes

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