Triethylamine → HCID 53719614, compound

HRID 1720537Notes

Reaction equation

HRID 1720537 reaction equation
Cl[C:2]([O:4][C:5](Cl)(Cl)Cl)=[O:3].[C:9]12(CO)[CH2:18][CH:13]3[CH2:14][CH:15]([CH2:17][CH:11]([CH2:12]3)[CH2:10]1)[CH2:16]2.C(N(CC)CC)C.[CH2:28]([O:35][C:36](=[O:42])[C@@H:37]1[CH2:41][CH2:40][CH2:39][NH:38]1)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C1COCC1.C(Cl)Cl.O>[CH2:28]([O:35][C:36](=[O:42])[C@@H:37]1[CH2:41][CH2:40][CH2:39][N:38]1[C:2]([O:4][CH2:5][C:9]12[CH2:10][CH:11]3[CH2:12][CH:13]([CH2:14][CH:15]([CH2:17]3)[CH2:16]1)[CH2:18]2)=[O:3])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

8

Reactant 4

HCID 8471Triethylamine2×HCID 10426DiphosgeneHCID 64556Tricyclo(3.3.1.1'3,7)dec-1-ylmethanolHCID 736155Benzyl L-prolinate

Product 1

HCID 53719614HCID 53719614, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of trichloromethyl chloroformate (0.36 ml) THF (40 ml) was dropwise added a solution of 1-adamantane methanol (1.00 g) and triethylamine (0.84 ml) in THF (20 ml) under ice-cooling. After stirring the mixture at room temperature for 1.5 hours, a solution of 1,-proline benzyl ester (1.45 g) in methylene chloride (15 ml) was added thereto, followed by dropwise addition of triethylamine (1.7 ml). After stirring the mixture at room temperature for 20 minutes, the reaction mixture was poured into water and extracted with ethyl acetate.

Workup

  1. temperaturecooling
  2. stirringAfter stirring the mixture at room temperature for 20 minutes
  3. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-e4a3ad9d75fe47d19ed1bdf231faa86a
Source dataset
uspto-grants-1996_04
Patent number
US05506256

Reaction notes

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