1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 10603610, compound

HRID 1078620Notes

Reaction equation

HRID 1078620 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[CH2:13][CH2:12][NH:11][C@H:10]([C:14](OC)=O)[C:9]1=[O:18])([CH3:4])([CH3:3])[CH3:2].[CH2:20]([O:27][C:28]([NH:30][C@H:31]([C:41]([OH:43])=O)[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.CN(C)CCCN=C=NCC>C(Cl)Cl>[C:1]([O:5][C:6](=[O:19])[CH2:7][N:8]1[CH2:13][CH2:12][N:11]([C:41](=[O:43])[C@H:31]([CH2:32][C:33]2[CH:34]=[CH:35][C:36]([O:39][CH3:40])=[CH:37][CH:38]=2)[NH:30][C:28]([O:27][CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:29])[C@@H:10]([CH2:14][C:6]([O:5][CH3:1])=[O:19])[C:9]1=[O:18])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 10496574(2S)-2-{[(benzyloxy)carbonyl]amino}-3-(4-methoxyphenyl)propanoic acidHCID 54380928HCID 54380928, compound

Product 1

HCID 10603610HCID 10603610, compoundYield 117.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 28.8 g of (S)-3-methoxycarbonyl-2-oxopiperazine-1-acetic acid t butyl ester, 23.0 g of N-benzyloxycarbonyl-O-methyl-L-tyrosine and 202 ml of methylene chloride, 15.3 g of 1-(3-dimethylaminopropyl)-3-ehtylcarbodiimide was added. The mixture was stirred for 2 hours and concentrated under reduced pressure. The residue was disolved in ethyl acetate. The solution was washed with a 5% aqueous solution of potassium hydrogensulfate and a saturated sodium hydrogen carbonate. The organic layer was concentrated under reduced pressure to give 37.0 g of crude (S)-4-(N-benzyloxycarbonyl-O-methyl-L-tyrosyl)-3-methoxycarbonylmethyl-2-oxopiperazine-1-acetic acid t butyl ester. This product was dissolved in 74.0 ml of methylene chloride, to which was added 74.0 ml of trifluoroacetic acid. The mixture was stirred for one hour at room temperature. The reaction solution was concentrated under reduced pressure. The residue was subjected to azeotropy with toluene several times to afford 39.12 g of the title compound as a colorless oily product.

Workup

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. washThe solution was washed with a 5% aqueous solution of potassium hydrogensulfate
  4. concentrationThe organic layer was concentrated under reduced pressure

Sources & evidence

ORD record
ord-1d33f771608348db9d946eac88496d79
Source dataset
uspto-grants-1996_08
Patent number
US05550131

Reaction notes

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