Dichloromethane → Ethyl 4-[14-(trimethylsilyl)tetradecylamino]hippurate

HRID 652031

Reaction equation

HRID 652031 reaction equation
Cl.[CH3:2][Si:3]([CH3:29])([CH3:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](Cl)=[O:24])=[CH:21][CH:20]=1.O1CCOCC1.[NH2:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39].C(Cl)Cl>CN(C)C1C=CN=CC=1.C(N(CC)CC)C>[CH3:2][Si:3]([CH3:29])([CH3:28])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][NH:18][C:19]1[CH:27]=[CH:26][C:22]([C:23](=[O:24])[NH:36][CH2:37][C:38]([O:40][CH2:41][CH3:42])=[O:39])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 12176Glycine ethyl esterHCID 312751,4-DioxaneHCID 201982304-[14-(Trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride

Product 1

HCID 20198242Ethyl 4-[14-(trimethylsilyl)tetradecylamino]hippurate

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 20 g. 4-[14-(trimethylsilyl)tetradecylamino]benzoyl chloride hydrochloride in 100 ml. dioxane is added to 4.9 g. freshly prepared ethyl glycinate in 300 ml. of methylene chloride containing 1 g. of 4-(dimethylamino)pyridine and 10 ml. of triethylamine. After 16 hours at room temperature the reaction is refluxed for 2 hours, cooled and filtered. The mother liquor is extracted with water and 10% hydrochloric acid. The solution is dried and concentrated in vacuo to an amber liquid. A sample is chromatographed on silica, appropriate fractions are pooled and evaporated to yield a solid which is recrystallized to a white solid.

Workup

  1. temperaturecooled
  2. filtrationfiltered
  3. extractionThe mother liquor is extracted with water and 10% hydrochloric acid
  4. customThe solution is dried
  5. concentrationconcentrated in vacuo to an amber liquid
  6. customA sample is chromatographed on silica, appropriate fractions
  7. customevaporated
  8. customto yield a solid which
  9. customis recrystallized to a white solid

Sources & evidence

ORD record
ord-6b5996995f4e4a588ac5b7b2229113ed
Source dataset
uspto-grants-1987_06
Patent number
US04670421

Linked notes

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