Triethylamine → HCID 54182767, compound

HRID 652035Notes

Reaction equation

HRID 652035 reaction equation
FC(F)(F)C([N:5]([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][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:6]1[CH:14]=[CH:13][C:9]([C:10](Cl)=[O:11])=[CH:8][CH:7]=1)=O.C(N(CC)CC)C.C([O:44][C:45](=[O:49])[C@H:46]([CH3:48])[NH2:47])C>CCOCC>[CH3:32][Si:29]([CH3:30])([CH3:31])[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][NH:5][C:6]1[CH:7]=[CH:8][C:9]([C:10]([NH:47][C@H:46]([C:45]([OH:49])=[O:44])[CH3:48])=[O:11])=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 76507L-Alanine ethyl esterHCID 20198247HCID 20198247, compound

Product 1

HCID 54182767HCID 54182767, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 4.64 g. of 4-[N-trifluoroacetyl-14-(trimethylsilyl)tetradecylamino]benzoyl chloride and 1.2 g. of triethylamine in 200 ml. of warm ether is treated with 1.55 g. alanine ethyl ester and refluxed for 24 hours. The hot solution is filtered, the residue is washed with hot ether, and the solution is evaporated. After treatment with aqueous methanolic potassium carbonate, the product is precipitated by acidification, filtered, and dried. Crystallization yields the product as a white, crystalline solid.

Workup

  1. filtrationThe hot solution is filtered
  2. washthe residue is washed with hot ether
  3. customthe solution is evaporated
  4. customAfter treatment with aqueous methanolic potassium carbonate, the product is precipitated by acidification
  5. filtrationfiltered
  6. customdried
  7. customCrystallization
  8. customyields the product as a white, crystalline solid

Sources & evidence

ORD record
ord-3dc12ac40cc54f768ec4a111ede1107f
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Reaction notes

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