Pyridine → HCID 15542338, compound

HRID 2308186Notes

Reaction equation

HRID 2308186 reaction equation
N1C=CC=CC=1.[NH2:7][C@H:8]([C:12]([N:14]1[CH2:36][CH2:35][CH2:34][C@H:15]1[C:16]([NH:18][C@@H:19]([CH:31]([CH3:33])[CH3:32])[CH:20]([C:22]1[O:23][C:24]2[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=2[N:26]=1)[OH:21])=[O:17])=[O:13])[CH:9]([CH3:11])[CH3:10].[C:37]([O:41][C:42]([CH2:44][N:45]1[C:50](=[O:51])[CH:49]=[CH:48][N:47]([CH2:52][C:53](O)=[O:54])[C:46]1=[O:56])=[O:43])([CH3:40])([CH3:39])[CH3:38].Cl.N=C=N>O>[C:37]([O:41][C:42]([CH2:44][N:45]1[C:50](=[O:51])[CH:49]=[CH:48][N:47]([CH2:52][C:53]([NH:7][C@H:8]([C:12]([N:14]2[CH2:36][CH2:35][CH2:34][C@H:15]2[C:16]([NH:18][C@@H:19]([CH:31]([CH3:32])[CH3:33])[CH:20]([C:22]2[O:23][C:24]3[CH:30]=[CH:29][CH:28]=[CH:27][C:25]=3[N:26]=2)[OH:21])=[O:17])=[O:13])[CH:9]([CH3:11])[CH3:10])=[O:54])[C:46]1=[O:56])=[O:43])([CH3:40])([CH3:38])[CH3:39]

Participants

6

Reactant 4

HCID 1049PyridineHCID 10364607HCID 10364607, compoundHCID 155423432-(3-Tert-butoxycarbonylmethyl-2,4-dioxo-1-pyrimidinyl)acetic acidHCID 21863233HCID 21863233, compound

Product 1

HCID 15542338HCID 15542338, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To pyridine (20 ml) containing L-valyl-N-[(1S)-2-(2-benzoxazolyl)-1-isopropyl-2-hydroxyethyl]-L-prolinamide (1.0 g) are added 2-(3-tert-butoxycarbonylmethyl-2,4-dioxo-1-pyrimidinyl)acetic acid (0.7 g) obtained in Example 4 and 1-ethyl-3-dimethylaminopropyl)carbodiimide hydrochloride (0.6 g), and the mixture is stirred at room temperature for 15 hours. The reaction solution is poured into water, and the mixture is extracted with ethyl acetate. The extract is washed successively with 1 mol/liter hydrochloric acid, a saturated aqueous sodium hydrogen carbonate solution, and a saturated brine, and dried over anhydrous magnesium sulfate. The solvent is removed by evaporation under reduced pressure to give the desired 2-(3-tert-butoxycarbonylmethyl-2,4-dioxo-1-pyrimidinyl)acetyl-L-valyl-N-[(1S)-2-(2-benzoxazolyl)-1-isopropyl-2-hydroxyethyl]-L-prolinamide (1.5 g) as powders.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed successively with 1 mol/liter hydrochloric acid
  3. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and a saturated brine, and dried over anhydrous magnesium sulfate
  4. customThe solvent is removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-2fce65e33572413e92c2c0423910287e
Source dataset
uspto-grants-2004_12
Patent number
US06835714B1

Reaction notes

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