Triethylamine → 2-{(R)-1-[N-Toluoyl-(3-phthalimido-2-oxo-propyl)amino]-2-methyl-propyl}-3-benzyl-7-chloro-chromen-4-one

HRID 473046Notes

Reaction equation

HRID 473046 reaction equation
[C:1]1(=[O:39])[N:5]([CH2:6][C:7](=[O:33])[CH2:8][NH:9][C@@H:10]([C:14]2[O:15][C:16]3[C:21]([C:22](=[O:31])[C:23]=2[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:20][CH:19]=[C:18]([Cl:32])[CH:17]=3)[CH:11]([CH3:13])[CH3:12])[C:4](=[O:34])[C:3]2=[CH:35][CH:36]=[CH:37][CH:38]=[C:2]12.CCN(CC)CC.[C:47]1([CH3:56])[C:48]([C:53](Cl)=[O:54])=[CH:49][CH:50]=[CH:51][CH:52]=1>C(Cl)Cl>[C:47]1([CH3:56])[C:48]([C:53]([N:9]([CH2:8][C:7](=[O:33])[CH2:6][N:5]2[C:4](=[O:34])[C:3]3=[CH:35][CH:36]=[CH:37][CH:38]=[C:2]3[C:1]2=[O:39])[C@@H:10]([C:14]2[O:15][C:16]3[C:21]([C:22](=[O:31])[C:23]=2[CH2:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)=[CH:20][CH:19]=[C:18]([Cl:32])[CH:17]=3)[CH:11]([CH3:13])[CH3:12])=[O:54])=[CH:49][CH:50]=[CH:51][CH:52]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 702762-Methylbenzoyl chlorideHCID 667559422-[(R)-1-(3-Phthalimido-2-oxo-propylamino)-2-methyl-propyl)-3-benzyl-7-chloro-chromen-4-one

Product 1

HCID 667559282-{(R)-1-[N-Toluoyl-(3-phthalimido-2-oxo-propyl)amino]-2-methyl-propyl}-3-benzyl-7-chloro-chromen-4-oneYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-[(R)-1-(3-phthalimido-2-oxo-propylamino)-2-methyl-propyl]-3-benzyl-7-chloro-chromen-4-one (0.88 g, 1.5 mMol) in CH2Cl2 (10 mL) was added Et3N (0.23 mL, 1.6 mMol) and toluoyl chloride (0.21 mL, 1.6 mMol). The reaction was stirred at RT for 18 h, concentrated under vacuum, taken up in EtOAc, washed with 1 N HCl, brine, dried (MgSO4) and evaporated to dryness. Purification by flash chromatography on silica gel (5-15% EtOAc/hexane) followed by trituration with pet. ether, filtration and drying under vacuum gave the title compound (0.89 g, 90%) as a white solid: MS (ES) m/e 661.2 (M+H)+.

Workup

  1. concentrationconcentrated under vacuum
  2. washwashed with 1 N HCl, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customPurification by flash chromatography on silica gel (5-15% EtOAc/hexane)
  6. filtrationfollowed by trituration with pet. ether, filtration
  7. customdrying under vacuum

Sources & evidence

ORD record
ord-14343dab43be45b28a5ae675e4526876
Source dataset
uspto-grants-2014_01
Patent number
US08633236B2

Reaction notes

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