Triethylamine → HCID 19700638, compound

HRID 861912Notes

Reaction equation

HRID 861912 reaction equation
[C:1]12([C:11](Cl)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.O=C1[N:21](CCC(C)C)[C:20]2[CH:27]=[CH:28][CH:29]=[CH:30][C:19]=2[N:18]([CH2:31][C:32]2[CH:37]=[CH:36][C:35]([O:38][CH3:39])=[CH:34][CH:33]=2)C(=O)C1=NNC1C=CC=CC=1.C(N(CC)CC)C>C1COCC1.C(OCC)(=O)C>[C:1]12([C:11]([NH:21][C:20]3[CH:27]=[CH:28][CH:29]=[CH:30][C:19]=3[NH:18][CH2:31][C:32]3[CH:33]=[CH:34][C:35]([O:38][CH3:39])=[CH:36][CH:37]=3)=[O:12])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 54325231HCID 54325231, compound

Product 1

HCID 19700638HCID 19700638, compoundYield 151.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-Adamantanecarbonyl chloride (1.91 g )) was dropped into a solution of intermediate 2 (1.83 g ) and triethylamine (1.45 ml) in dry THF (100 ml at 23°, under a nitrogen atmosphere. The mixture was stirred at reflux for 3 h, allowed to cool to 20°, then diluted with ethyl acetate (120 ml) washed with brine (150 ml), dried, and concentrated in vacuo. This material (3.21 g) was crystallised from DCM/CH to give the title compound as a white solid (2.3 g). T.l.c. CH-EA (8:2), Rf 0.34 IR:3393, 3304 (NH) cm-1.

Workup

  1. temperatureat reflux for 3 h
  2. temperatureto cool to 20°
  3. washwashed with brine (150 ml)
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThis material (3.21 g) was crystallised from DCM/

Sources & evidence

ORD record
ord-2719463c782a4ba881b360efe37fd578
Source dataset
uspto-grants-1998_02
Patent number
US05716953

Reaction notes

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