1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → [4-(8-Ethyl-2,2,4,4-tetramethyl-chroman-6-yl-ethynyl) phenyl]acetic acid

HRID 24126Notes

Reaction equation

C12(C=CC3C=C(C(O)=O)C=CC=3O1)CC2.C[O:17][C:18](=[O:46])[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]#[C:27][C:28]2[CH:29]=[C:30]([CH:42]3C[CH2:43]3)[C:31]3[O:38][C:35]4([CH2:37][CH2:36]4)[CH2:34][C:33]([CH3:40])([CH3:39])[C:32]=3[CH:41]=2)=[CH:22][C:21]=1F.C(OC(=O)CC1C=CC=C(O)C=1)(C)(C)C.Cl.CN(C)CCCN=C=NCC>ClCCl.CN(C)C1C=CN=CC=1.CCCCCC.C(OCC)(=O)C>[CH2:42]([C:30]1[CH:29]=[C:28]([C:27]#[C:26][C:23]2[CH:24]=[CH:25][C:20]([CH2:19][C:18]([OH:46])=[O:17])=[CH:21][CH:22]=2)[CH:41]=[C:32]2[C:31]=1[O:38][C:35]([CH3:36])([CH3:37])[CH2:34][C:33]2([CH3:40])[CH3:39])[CH3:43]

Participants

Procedure

A solution of spiro[2H-1-benzopyran-2,1′-cyclopropane]-6-carboxylic acid, 8-cyclopropyl-3,4-dihydro-4,4-dimethyl- (Intermediate 49, 0.05 g, 0.18 mmol) in anhydrous dichloromethane (5 mL) was treated with tert-butyl-3-hydroxy phenyl acetate (Reagent F, 0.04 g, 0.18 mmol) followed by 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.029 g, 0.1 mmol) and 4-dimethylaminopyridine (0.022 g, 0.18 mmol). The resulting solution was stirred at ambient temperature overnight. The reaction mixture was subjected to flash column chromatography over silica gel (230-400 mesh) using 7% ethyl acetate in hexane as the eluent to afford the title compound as a clear oil that solidified on standing (0.020 g, 23%).

Sources & evidence

ORD record: ord-65cff2dfe3874250a33c243d6ee357a0
Source dataset: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06855512B2

Reaction notes

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Reaction equation

Participants

Reactant 4

Product 1

Reagents, catalysts & solvents 4

Procedure

Sources & evidence

Reaction notes