Triethylamine → HCID 11383956, compound

HRID 1583241Notes

Reaction equation

HRID 1583241 reaction equation
OC1C=CC(C(N[C@H](C(N[C@H](C(O)=O)CC2C=CC=CC=2)=O)C)=O)=CC=1.C(N(CC)CC)C.[CH2:34]([O:36][C:37](=[O:47])[C@H:38]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH2:39])[CH3:35].Cl.[C:49]([NH:59][C@H:60]([C:62](O)=[O:63])[CH3:61])([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50]>ClCCl>[CH2:34]([O:36][C:37](=[O:47])[C@H:38]([CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)[NH:39][C:62](=[O:63])[C@H:60]([CH3:61])[NH:59][C:49]([O:51][CH2:52][C:53]1[CH:58]=[CH:57][CH:56]=[CH:55][CH:54]=1)=[O:50])[CH3:35]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 165085Ethyl L-phenylalaninate hydrochlorideHCID 736104N-carbobenzyloxyalanineHCID 7019742HCID 7019742, compound

Product 1

HCID 11383956HCID 11383956, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Synthesis of p-hydroxybenzoyl-L-alanyl-L-phenylalanine: 0.1 g (0.1 mol) of triethylamine was added to a suspension of 23.0 g (0.1 mol) of L-phenylalanine ethyl ester·HCl in 500 ml of dichloromethane, and to this mixture in an ice bath was added 22.3 g (0.1 mol) of carbobenzoxy-L-alanine, and then 19.2 g (0.1 mol) of 1-ethyl-3(3-dimethyaminopropyl) carbodiimide·HCl was added to the mixture. This mixture was stirred for three hours. This reaction mixture was washed with a 0.1% aqueous solution of Na2CO3 three times and with a 0.1 N HCl solution three times, and then with distilled water three times. Thereafter, the mixture was dried over anhydrous sodium sulfate, and dichloromethane was removed from the mixture under reduced pressure to obtain carbobenzoxy-L-alanyl-L-phenylalanine ethyl ester. This ester was dissolved in 260 ml of 25% HBr in glacial acetic acid, and this solution was stirred for one hour. To this solution was added 5 l of absolute ethyl ether to produce a precipitate. The precipitate was filtered and washed with ethyl ether to obtain L-alanyl-L-phenylalanine ethyl ester·HBr.

Workup

  1. washThis reaction mixture was washed with a 0.1% aqueous solution of Na2CO3 three times and with a 0.1 N HCl solution three times
  2. dry with materialThereafter, the mixture was dried over anhydrous sodium sulfate, and dichloromethane
  3. customwas removed from the mixture under reduced pressure

Sources & evidence

ORD record
ord-b71bae26336a4fc1af018dfc7e2df47f
Source dataset
uspto-grants-1985_11
Patent number
US04551272

Reaction notes

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