Dichloromethane → HCID 12137004, compound

HRID 898664Notes

Reaction equation

HRID 898664 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:17]([OH:19])=[O:18])[CH:6]=[C:7]2[C:12]=1[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]2([CH3:16])[CH3:15])#[CH:2].Cl[CH2:21]Cl.C(O[C:27]1[CH:32]=[CH:31][C:30](O)=[C:29](C(C)(C)C)[C:28]=1[F:38])(=O)C.Cl.CN(C)[CH2:42][CH2:43][CH2:44]N=C=NCC.[C:51]([O:54]CC)(=[O:53])[CH3:52]>CN(C)C1C=CN=CC=1.CCCCCC>[F:38][C:28]1[CH:27]=[C:32]([O:18][C:17]([C:5]2[CH:6]=[C:7]3[C:12](=[C:3]([C:1]#[CH:2])[CH:4]=2)[O:11][C:10]([CH3:14])([CH3:13])[CH2:9][C:8]3([CH3:15])[CH3:16])=[O:19])[CH:31]=[CH:30][C:29]=1[CH2:52][C:51]([O:54][C:43]([CH3:42])([CH3:44])[CH3:21])=[O:53]

Participants

8

Reactant 5

HCID 6344DichloromethaneHCID 8857Ethyl AcetateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 12137002HCID 12137002, compound2×HCID 86589928HCID 86589928, compound

Product 1

HCID 12137004HCID 12137004, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8058HexaneSolvent

Procedure

Following General Procedure D and using 8-ethynyl-2,2,4,4-tetramethyl chroman-6-carboxylic acid (Compound 26, 0.107 g, 0.415 mmol), anhydrous dichloromethane (10 mL), tert-butyl-2-fluoro-4-hydroxy phenyl acetate (Compound 14, 0.14 g, 0.62 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.12 g, 0.62 mmol) and 4-(dimethylamino)pyridine (0.101 g, 0.83 mmol) followed by flash column chromatography over silica gel (230-400 mesh) using 10-15% ethyl acetate in hexane as the eluent, the title compound was obtained as a pale yellow solid (0.156 g, 92%).

Sources & evidence

ORD record
ord-3194904e730d400283aca438c9fbd7ac
Source dataset
uspto-grants-2008_04
Patent number
US07351737B2

Reaction notes

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