Triethylamine → HCID 13385090, compound

HRID 2418182Notes

Reaction equation

HRID 2418182 reaction equation
[C:1]([NH:11][C@H:12]([C:14]([OH:16])=O)[CH3:13])([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].C(N(CC)CC)C.C(Cl)(=O)OCC.[C:30]([O:34][C:35](=[O:58])[C@H:36]([CH2:51][C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1)[NH:37][C:38](=[O:50])[CH2:39][NH:40][CH:41]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42]1)([CH3:33])([CH3:32])[CH3:31]>O1CCCC1.C(Cl)(Cl)Cl.O>[C:30]([O:34][C:35](=[O:58])[C@H:36]([CH2:51][C:52]1[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=1)[NH:37][C:38](=[O:50])[CH2:39][N:40]([C:14](=[O:16])[C@H:12]([CH3:13])[NH:11][C:1]([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2])[CH:41]1[CH2:49][C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH2:42]1)([CH3:33])([CH3:31])[CH3:32]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 736104N-carbobenzyloxyalanineHCID 13385088HCID 13385088, compound

Product 1

HCID 13385090HCID 13385090, compoundYield 94.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

N-Carbobenzoxy-L-alanine (3.5 g) and triethylamine (1.6 g) are dissolved in 50 ml of tetrahydrofuran, followed by dropwise addition of 1.7 g of ethyl chlorocarbonate with stirring at -15° C. After completion of addition, the mixture is stirred for 15 minutes and, a solution of 3.9 g of N-(2-indanyl)glycyl-L-phenylalanine tert-butyl ester in 100 ml of chloroform is added dropwise at -10° C. The mixture is stirred at room temperature for one hour and poured into 50 ml of water. The chloroform layer is separated and distilled. The residue is dissolved in 200 ml of ethyl acetate. The solution is washed twice with 50 ml portions of 1N sodium hydroxide, once with 50 ml of water, twice with 50 ml portions of 10% aqueous solution of phosphoric acid, and once with 50 ml of water in that order. It is then dried over anhydrous magnesium sulfate and distilled to give 5.6 g of N-carbobenzoxy-L-alanyl-N-(2-indanyl)glycyl-L-phenylalanine tert-butyl ester as an oil.

Workup

  1. additionAfter completion of addition
  2. stirringthe mixture is stirred for 15 minutes
  3. stirringThe mixture is stirred at room temperature for one hour
  4. customThe chloroform layer is separated
  5. distillationdistilled
  6. dissolutionThe residue is dissolved in 200 ml of ethyl acetate
  7. washThe solution is washed twice with 50 ml portions of 1N sodium hydroxide, once with 50 ml of water, twice with 50 ml portions of 10% aqueous solution of phosphoric acid
  8. dry with materialIt is then dried over anhydrous magnesium sulfate
  9. distillationdistilled

Sources & evidence

ORD record
ord-6dd75f1fa2224b0b9c516333e96ec3ac
Source dataset
uspto-grants-1984_09
Patent number
US04472383

Reaction notes

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