Triethylamine → HCID 67842500, compound

HRID 1729108Notes

Reaction equation

HRID 1729108 reaction equation
[CH3:1][O:2][C:3](=[O:17])[C@:4]([CH3:16])([CH2:6][C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[CH:9][N:8]=1)[NH2:5].Cl[C:19]([O:21][CH:22]1[CH:29]2[CH2:30][CH:25]3[CH2:26][CH:27]([CH2:31][CH:23]1[CH2:24]3)[CH2:28]2)=[O:20].C(N(CC)CC)C>C1COCC1>[CH3:1][O:2][C:3](=[O:17])[C@:4]([CH3:16])([CH2:6][C:7]1[N:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]2=[CH:9][N:8]=1)[NH:5][C:19]([O:21][CH:22]1[CH:23]2[CH2:31][CH:27]3[CH2:26][CH:25]([CH2:30][CH:29]1[CH2:28]3)[CH2:24]2)=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 108785372-adamantyl ChloroformateHCID 54365445HCID 54365445, compound

Product 1

HCID 67842500HCID 67842500, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a stirred solution of the crude compound of Step 3 (0.83 g, 3.56 mmol) in dry THF (10 mL) was added a solution of 2-adamantyl chloroformate (0.80g, 3.7 mmol) in dry THF (3 mL) followed by a solution of triethylamine (0.38 g, 3.8 mmol) in dry THF (5 mL) dropwise. After 2 hours stirring, thereaction mixture was filtered, and the solvent removed in vacuo to give theproduct (1.2 g, 82%) as a colorless amorphous solid, which was used withoutfurther purification; IR (KBr) 1737 and 1699 cm-1.

Workup

  1. filtrationmixture was filtered
  2. customthe solvent removed in vacuo
  3. customto give theproduct (1.2 g, 82%) as a colorless amorphous solid, which
  4. customwas used withoutfurther purification

Sources & evidence

ORD record
ord-1d0a9465562d47e792f6d61908b36388
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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