Water → HCID 19612287, compound

HRID 1602703Notes

Reaction equation

HRID 1602703 reaction equation
[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14]3([CH3:26])[C:18]4[CH:19]=[C:20]([C:23](O)=[O:24])[CH:21]=[CH:22][C:17]=4[O:16][CH2:15]3)[CH:5]=[CH:4][C:3]1=2.ON1C2C=CC=CC=2N=N1.[NH:38]1[CH2:43][CH2:42][O:41][CH2:40][CH2:39]1.O>C1COCC1.CN(C=O)C.C(OCC)(=O)C>[CH3:1][C:2]1([CH3:27])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]3([CH3:26])[C:18]4[CH:19]=[C:20]([C:23]([N:38]5[CH2:43][CH2:42][O:41][CH2:40][CH2:39]5)=[O:24])[CH:21]=[CH:22][C:17]=4[O:16][CH2:15]3)[CH:5]=[CH:4][C:3]1=2

Participants

8

Reactant 4

HCID 962WaterHCID 8083MorpholineHCID 757711-HydroxybenzotriazoleHCID 15840104HCID 15840104, compound

Product 1

HCID 19612287HCID 19612287, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)-3-methyl-2H-1-benzofuran-5-carboxylic acid (100 mg, 0.275 mmol), 1-hydroxybenzotriazole (74 mg, 0.55 mmol) 1,3-dicyclohexylcarbodiimide (112 mg, 0.55 mmol) and morpholine (0.024 ml, 0.255 mmol) in 5 ml of THF and 2 ml of DMF is stirred at room temperature for 6 hours. 30 ml of water and 30 ml of ethyl acetate are added. After stirring and separation of the phases by settling, the aqueous phase is extracted with 2×30 ml of ethyl acetate. The organic phases are then combined and washed twice with 30 ml of water and then dried over magnesium sulphate and concentrated on a rotary evaporator under vacuum at 40° C. The product is then purified by flash chromatography on a column of silica (50% heptane/50% ethyl acetate).

Workup

  1. customseparation of the phases
  2. extractionthe aqueous phase is extracted with 2×30 ml of ethyl acetate
  3. washwashed twice with 30 ml of water
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated on a rotary evaporator under vacuum at 40° C
  6. customThe product is then purified by flash chromatography on a column of silica (50% heptane/50% ethyl acetate)

Sources & evidence

ORD record
ord-2f44f52f716d405f9c58628db042d7b2
Source dataset
uspto-grants-1999_11
Patent number
US05981776

Reaction notes

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