2-(Dimethylamino)ethanol → HCID 69320189, compound

HRID 2055052Notes

Reaction equation

HRID 2055052 reaction equation
[C:1]([Si:5]([CH3:38])([CH3:37])[O:6][C:7]1[CH:8]=[CH:9][C:10]2[C:11]3[CH:24]([CH2:25][C:26]([OH:28])=[O:27])[O:23][C:22]4[CH:21]=[C:20]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH:19]=[CH:18][C:17]=4[C:12]=3[CH2:13][O:14][C:15]=2[CH:16]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42]O.CC(C)N=C=NC(C)C>CN(C1C=CN=CC=1)C.C(Cl)Cl>[CH3:39][N:40]([CH3:44])[CH2:41][CH2:42][O:27][C:26](=[O:28])[CH2:25][CH:24]1[C:11]2[C:10]3[CH:9]=[CH:8][C:7]([O:6][Si:5]([C:1]([CH3:2])([CH3:4])[CH3:3])([CH3:38])[CH3:37])=[CH:16][C:15]=3[O:14][CH2:13][C:12]=2[C:17]2[CH:18]=[CH:19][C:20]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:31])[CH3:32])=[CH:21][C:22]=2[O:23]1

Participants

6

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 12734DiisopropylcarbodiimideHCID 21959303HCID 21959303, compound

Product 1

HCID 69320189HCID 69320189, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of [2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-acetic acid, the compound prepared as in Example 95 above, (56 mg, 0.1 mmol), 2-dimethylamino-ethanol (30 μL, 27 mg, 3.0 eq.), DIC (14 mg, 18 μL) and DMAP (12 mg) in DCM (2 mL) was stirred for 13 hours. The reaction mixture was then concentrated to yield [2,8-Bis-(tert-butyl-dimethyl-silyloxy)-5,11-dihydro-chromeno[4,3-c]chromen-5-yl]-acetic acid 2-dimethylamino-ethyl ester as a crude foam.

Workup

  1. concentrationThe reaction mixture was then concentrated

Sources & evidence

ORD record
ord-e206d64848144421be2fcd238fe90766
Source dataset
uspto-grants-2008_02
Patent number
US07329654B2

Reaction notes

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