Triethylamine → 1-adamantylcarbonyl-L-alanyl-L-proline anilide

HRID 1448733Notes

Reaction equation

HRID 1448733 reaction equation
Br.[NH2:2][C@H:3]([C:5]([N:7]1[CH2:20][CH2:19][CH2:18][C@H:8]1[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])=[O:6])[CH3:4].C(N(CC)CC)C.[C:28]12([C:38](Cl)=[O:39])[CH2:37][CH:32]3[CH2:33][CH:34]([CH2:36][CH:30]([CH2:31]3)[CH2:29]1)[CH2:35]2>O1CCCC1>[C:28]12([C:38]([NH:2][C@H:3]([C:5]([N:7]3[CH2:20][CH2:19][CH2:18][C@H:8]3[C:9]([NH:11][C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)=[O:10])=[O:6])[CH3:4])=[O:39])[CH2:35][CH:34]3[CH2:33][CH:32]([CH2:31][CH:30]([CH2:36]3)[CH2:29]1)[CH2:37]2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 989151-Adamantanecarbonyl chlorideHCID 22809936L-alanyl-L-proline anilide hydrobromide

Product 1

HCID 322978541-adamantylcarbonyl-L-alanyl-L-proline anilide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

3.42 g (0.01 mol) of L-alanyl-L-proline anilide hydrobromide were suspended in 100 ml of dry tetrahydrofuran and the suspension was cooled to 0° C. There were then added 2.8 ml (0.02 mol) of triethylamine followed by 1.72 g (0.001 mol) of 1-adamantoyl chloride. The mixture was stirred at 0° C. for 0.5 hour and at room temperature for 2 hours and then evaporated. The residue was extracted twice with 40 ml of ethyl acetate each time. The combined ethyl acetate extracts were washed successively with two 20 ml portions of 1-N hydrochloric acid, 20 ml of water, two 20 ml portions of 5% sodium bicarbonate solution and two 20 ml portions of water, dried over magnesium sulphate and evaporated. The residue was crystallised from ether/petroleum ether and further purified by chromatography on 100 g of silica gel using chloroform for the elution. Evaporation of the chloroform eluate and crystallisation of the residue from ether/petroleum ether yielded 1.09 g (24%) of pure N-(1-adamantylcarbonyl-L-alanyl-L-proline anilide of melting point 119°-121° C.; [α]D20 =-142.9° (c=1% in methanol).

Workup

  1. customevaporated
  2. extractionThe residue was extracted twice with 40 ml of ethyl acetate each time
  3. washThe combined ethyl acetate extracts were washed successively with two 20 ml portions of 1-N hydrochloric acid, 20 ml of water, two 20 ml portions of 5% sodium bicarbonate solution and two 20 ml portions of water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customThe residue was crystallised from ether/petroleum ether
  7. customfurther purified by chromatography on 100 g of silica gel
  8. washfor the elution
  9. customEvaporation of the chloroform eluate and crystallisation of the residue from ether/petroleum ether

Sources & evidence

ORD record
ord-d2b31c78dd014162af2c59c1170709a5
Source dataset
uspto-grants-1980_02
Patent number
US04187216

Reaction notes

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