Dimethylformamide → Allyl (1-{4-[dihydroxy-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)-carbamate

HRID 1921672Notes

Reaction equation

HRID 1921672 reaction equation
[CH2:1]([O:4][C:5]([NH:7][C:8]1([C:11]2[CH:19]=[CH:18][C:14]([C:15](O)=O)=[CH:13][CH:12]=2)[CH2:10][CH2:9]1)=[O:6])[CH:2]=[CH2:3].CN(C([O:27]N1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[O:42]1[C:50]2[C:45](=C[CH:47]=[CH:48][CH:49]=2)[CH2:44][C:43]1=[O:51].[H-].[Na+].CN([CH:57]=[O:58])C>O.C(O)(=O)C.C(N(CC)CC)C>[OH:27][C:47]1[CH:48]=[CH:49][C:50]2[O:42][C:43](=[O:51])[C:44](=[CH:15][C:14]3[CH:18]=[CH:19][C:11]([C:8]4([NH:7][C:5](=[O:6])[O:4][CH2:1][CH:2]=[CH2:3])[CH2:10][CH2:9]4)=[CH:12][CH:13]=3)[C:45]=2[C:57]=1[OH:58]

Participants

9

Reactant 5

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 683822(3H)-BenzofuranoneHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 593058104-(1-{[(Prop-2-en-1-yloxy)carbonyl]amino}cyclopropyl)benzoic acid

Product 1

HCID 131729705Allyl (1-{4-[dihydroxy-(2-oxobenzofuran-3-ylidene)methyl]phenyl}cyclopropyl)-carbamate

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8471TriethylamineSolvent

Procedure

0.8 g of 4-(1-allyloxycarbonylaminocyclopropyl)benzoic acid and 0.585 mL of triethylamine were dissolved in 10 mL of anhydrous DMF and combined with 1.16 g of TBTU, stirred for 15 minutes at RT, then combined with 0.4 g of coumaranone and stirred for a further 10 minutes. While cooling with the ice bath, 0.42 g of NaH was added batchwise as a 60% suspension in white oil, the mixture was stirred for 2 hours at RT and, once the reaction had ended, the mixture was diluted with water to a total volume of approximately 150 mL. The mixture was acidified with 2N acetic acid. The crystals were suction filtered and washed with water. Yield: 1.1 g of solid with a melting point of 125° C.-126° C.

Workup

  1. stirringstirred for a further 10 minutes
  2. stirringthe mixture was stirred for 2 hours at RT
  3. filtrationfiltered
  4. washwashed with water

Sources & evidence

ORD record
ord-e23e4cda0c624d55ba0ad7ce5b26d6f4
Source dataset
uspto-grants-2012_05
Patent number
US08173699B2

Reaction notes

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