Dicyclohexylcarbodiimide → HCID 178446735, compound

HRID 1252841Notes

Reaction equation

HRID 1252841 reaction equation
[C:1]1([CH2:7][O:8][C:9]([NH:11][CH:12]([PH:17](=[O:19])[OH:18])[CH2:13][CH2:14][CH2:15][CH3:16])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O[C@@H:21]([CH3:39])[C:22]([N:24]1[CH2:38][CH2:37][CH2:36][C@H:25]1[C:26]([O:28][CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)=[O:27])=[O:23].C1(N=C=NC2CCCCC2)CCCCC1.CN(C1C=CC=CN=1)C>O1CCCC1>[C:1]1([CH2:7][O:8][C:9]([NH:11][CH:12]([PH:17]([O:18][CH:21]([CH3:39])[C:22]([N:24]2[CH2:38][CH2:37][CH2:36][C@H:25]2[C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])=[O:23])=[O:19])[CH2:13][CH2:14][CH2:15][CH3:16])=[O:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 218852-DimethylaminopyridineHCID 133352881-[(S)-2-Hydroxy-1-oxopropyl]-L-proline, phenylmethyl esterHCID 178446733HCID 178446733, compound

Product 1

HCID 178446735HCID 178446735, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-[[(phenylmethoxy)carbonyl]amino]pentylphosphinic acid (490 mg., 1.72 mmole) and 1-[(S)-2-hydroxy-1-oxopropyl]-L-proline, phenylmethyl ester (255 mg., 0.92 mmole) in dry tetrahydrofuran (5 ml.) is treated with dicyclohexylcarbodiimide (285 mg., 1.38 mmole) and dimethylaminopyridine (50 mg.) and stirred at room temperature for 2.5 hours. The mixture is filtered, diluted with ethyl acetate, and washed successively with 5% potassium bisulfate, saturated sodium bicarbonate, and saturated sodium chloride solutions, dried over sodium sulfate, and evaporated to give crude (S)-1-[2-[[[1-[[(phenylmethoxy)carbonyl]amino]pentyl]phosphinyl]oxy]-1-oxopropyl]-L-proline, phenylmethyl ester.

Workup

  1. filtrationThe mixture is filtered
  2. additiondiluted with ethyl acetate
  3. washwashed successively with 5% potassium bisulfate, saturated sodium bicarbonate, and saturated sodium chloride solutions
  4. dry with materialdried over sodium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-2232f2c2c60d4618b5cdcd7f3c5f988b
Source dataset
uspto-grants-1988_05
Patent number
US04745196

Reaction notes

Loading…