Dicyclohexylcarbodiimide → HCID 22827564, compound

HRID 2417870Notes

Reaction equation

HRID 2417870 reaction equation
[CH3:1][N:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:3]([C:5]([OH:7])=O)[CH3:4].[NH:18]1[CH2:29][CH2:28][CH2:27][C@H:19]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].O.OC1C2N=NNC=2C=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>O1CCCC1>[CH3:1][N:2]([C:8]([O:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:9])[C@H:3]([C:5]([N:18]1[CH2:29][CH2:28][CH2:27][C@H:19]1[C:20]([O:22][C:23]([CH3:25])([CH3:26])[CH3:24])=[O:21])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 6453108L-Proline 1,1-dimethylethyl esterHCID 7016365Z-N-Me-Ala-OHHCID 178526939HCID 178526939, compound

Product 1

HCID 22827564HCID 22827564, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-methyl-N-[(phenylmethoxy)carbonyl]-L-alanine (4.74 g., 20 mmole) in distilled tetrahydrofuran (50 ml.) is added L-proline, 1,1-dimethylethyl ester (3.42 g., 20 mmole), hydroxybenzotriazole hydrate (3.06 g., 20 mmole) and dicyclohexylcarbodiimide (4.12 g., 20 mmole). The reaction mixture is stirred overnight, the precipitated dicyclohexylurea is filtered off, and the filtrate is concentrated. The residue is dissolved in ethyl acetate (50 ml.) and washed with saturated sodium bicarbonate (twice), 10% potassium bisulfate (twice), and water (twice), dried (Na2SO4), and concentrated to give 6.4 g. of 1-[N-methyl-N-[(phenylmethoxy)carbonyl]-L-alanyl]-L-proline,1,1-dimethylethyl esters as an oily residue.

Workup

  1. filtrationthe precipitated dicyclohexylurea is filtered off
  2. concentrationthe filtrate is concentrated
  3. dissolutionThe residue is dissolved in ethyl acetate (50 ml.)
  4. washwashed with saturated sodium bicarbonate (twice), 10% potassium bisulfate (twice), and water (twice),
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customto give 6.4 g

Sources & evidence

ORD record
ord-301221a4202542a0b7f620111618f336
Source dataset
uspto-grants-1984_09
Patent number
US04470973

Reaction notes

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