Dichloromethane → 2-(3-tert-butoxycarbonylmethyl-2,4-dioxo-1-pyrimidinyl)acetyl-L-valyl-N-[(1S)-2-(2-benzoxazolyl)-1-isopropyl-2-oxoethyl]-L-prolinamide

HRID 2308187Notes

Reaction equation

HRID 2308187 reaction equation
C(Cl)Cl.[C:4]([O:8][C:9]([CH2:11][N:12]1[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH2:19][C:20]([NH:22][C@H:23]([C:27]([N:29]2[CH2:51][CH2:50][CH2:49][C@H:30]2[C:31]([NH:33][C@@H:34]([CH:46]([CH3:48])[CH3:47])[CH:35]([C:37]2[O:38][C:39]3[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=3[N:41]=2)[OH:36])=[O:32])=[O:28])[CH:24]([CH3:26])[CH3:25])=[O:21])[C:13]1=[O:52])=[O:10])([CH3:7])([CH3:6])[CH3:5].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(O)(C)(C)C>[C:4]([O:8][C:9]([CH2:11][N:12]1[C:17](=[O:18])[CH:16]=[CH:15][N:14]([CH2:19][C:20]([NH:22][C@H:23]([C:27]([N:29]2[CH2:51][CH2:50][CH2:49][C@H:30]2[C:31]([NH:33][C@@H:34]([CH:46]([CH3:47])[CH3:48])[C:35]([C:37]2[O:38][C:39]3[CH:45]=[CH:44][CH:43]=[CH:42][C:40]=3[N:41]=2)=[O:36])=[O:32])=[O:28])[CH:24]([CH3:26])[CH3:25])=[O:21])[C:13]1=[O:52])=[O:10])([CH3:7])([CH3:6])[CH3:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 15542338HCID 15542338, compound

Product 1

HCID 155423402-(3-tert-butoxycarbonylmethyl-2,4-dioxo-1-pyrimidinyl)acetyl-L-valyl-N-[(1S)-2-(2-benzoxazolyl)-1-isopropyl-2-oxoethyl]-L-prolinamideYield 80.2%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

To methylene chloride (30 ml) containing 2-(3-tert-butoxy-carbonylmethyl-2,4-dioxo-1-pyrimidinyl)acetyl-L-valyl-N-[(1S)-2-(2-benzoxazolyl)-1-isopropyl-2-hydroxyethyl]-L-prolinamide (1.5 g) obtained in Example 9 are added t-butyl alcohol (0.16 g) and a Dess-Martin reagent (1.9 g), and the mixture is stirred at room temperature for one hour. The reaction solution is poured into a saturated aqueous sodium thiosulfate solution, and the mixture is extracted with ethyl acetate. The extract is washed successively with a saturated aqueous sodium thiosulfate solution, 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-oxoethyl]-L-prolinamide (1.2 g) as powders.

Workup

  1. extractionthe mixture is extracted with ethyl acetate
  2. washThe extract is washed successively with a saturated aqueous sodium thiosulfate solution
  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-1cab4c216530498ca6d2476b0d4b25ba
Source dataset
uspto-grants-2004_12
Patent number
US06835714B1

Reaction notes

Loading…