Water → HCID 18920517, compound

HRID 1291721Notes

Reaction equation

HRID 1291721 reaction equation
Cl[CH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1.[C:13]([O:17][C:18]([NH:20][CH2:21][CH2:22][CH2:23][N:24]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][N:33]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:34][CH2:35][CH2:36][NH:37][C:38]([O:40][C:41]([CH3:44])([CH3:43])[CH3:42])=[O:39])=[O:19])([CH3:16])([CH3:15])[CH3:14].[CH3:59][C:60]([CH3:63])([O-])[CH3:61].[K+].O>CN(C)P(N(C)C)N(C)C>[C:3]1([CH2:2][N:37]([C:38]([O:40][C:41]([CH3:42])([CH3:43])[CH3:44])=[O:39])[CH2:36][CH2:35][CH2:34][N:33]([C:45]([O:47][C:48]([CH3:51])([CH3:50])[CH3:49])=[O:46])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][N:24]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:23][CH2:22][CH2:21][N:20]([CH2:59][C:60]2[C:63]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:12]=[CH:11][CH:61]=2)[C:18]([O:17][C:13]([CH3:14])([CH3:15])[CH3:16])=[O:19])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 68451-ChloromethylnaphthaleneHCID 14585891HCID 14585891, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18920517HCID 18920517, compound

Reagents, catalysts & solvents 1

HCID 15355Hexamethylphosphorous triamideSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 1-chloromethylnaphthalene (1.7 g - 9.6 mmol) in 5 ml hexamethylphosphorous triamide (HMPA) is added to a mixture of 1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane (2.6 g) and potassium t-butoxide (1.07 gm) in HMPA (50 ml). The mixture is heated in an 80° C. oil bath for 4 hours, poured into 300 ml of water, and the aqeuous mixture is extracted with ethyl acetate (2×300 ml). The combined extracts are extracted with water (3×300 ml) and brine (300 ml). The organic layer is dried, evaporated and the residue is chromatographed (flash-silica gel column eluting with 4 to 1 toluene/ethylacetate to yield 800 mg of 1,18-bis-[(1-naphthyl)methyl]-1,5,14,18-tetra(t-butoxycarbonyl)-1,5,14,18-tetraazaoctadecane.

Workup

  1. extractionthe aqeuous mixture is extracted with ethyl acetate (2×300 ml)
  2. extractionThe combined extracts are extracted with water (3×300 ml) and brine (300 ml)
  3. customThe organic layer is dried
  4. customevaporated
  5. customthe residue is chromatographed (flash-silica gel column
  6. washeluting with 4 to 1 toluene/ethylacetate

Sources & evidence

ORD record
ord-04da8da406844509be775ee66f2e1a5d
Source dataset
uspto-grants-1998_05
Patent number
US05753714

Reaction notes

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