1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 58742306, compound

HRID 1988095Notes

Reaction equation

HRID 1988095 reaction equation
[CH2:1]([C@@:3]12[CH2:16][C@H:15]([OH:17])[C@:14]([OH:21])([C:18]#[C:19][CH3:20])[CH2:13][C@H:12]1[CH2:11][CH2:10][C:9]1[CH:8]=[C:7]([C:22](O)=[O:23])[CH:6]=[CH:5][C:4]2=1)[CH3:2].C(N(C(C)C)CC)(C)C.CN(C)CCCN=C=NCC.ON1C2C=CC=CC=2N=N1.[CH3:55][C:56]1[C:61]([CH2:62][NH2:63])=[CH:60][CH:59]=[CH:58][N:57]=1>O1CCCC1>[CH3:55][C:56]1[C:61]([CH2:62][NH:63][C:22]([C:7]2[CH:6]=[CH:5][C:4]3[C@@:3]4([CH2:1][CH3:2])[C@@H:12]([CH2:13][C@@:14]([OH:21])([C:18]#[C:19][CH3:20])[C@@H:15]([OH:17])[CH2:16]4)[CH2:11][CH2:10][C:9]=3[CH:8]=2)=[O:23])=[CH:60][CH:59]=[CH:58][N:57]=1

Participants

7

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 11434939(2-methylpyridin-3-yl)methanamineHCID 68830908HCID 68830908, compound

Product 1

HCID 58742306HCID 58742306, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (6S,7R,4bR,8aR)-4b-ethyl-6,7-dihydroxy-7-prop-1-ynyl-4b,5,6,7,8,8a,9,10-octahydro-phenanthrene-2-carboxylic acid (20 mg, 0.061 mmol) in tetrahydrofuran (2 mL) was added sequentially diisopropylethylamine (0.042 mL, 0.24 mmol), 1-[3-(dimethylamino)propyl]-3-ethyl carbodiimide (14 mg, 0.073 mmol), 1-hydroxybenzotriazole (9 mg, 0.064 mmol) and C-(2-methylpyridin-3-yl)-methylamine (0.025 mL, approximately 0.2 mmol). The mixture was stirred at room temperature for 1 day and was then quenched with saturated aqueous ammonium chloride solution. After extracting twice with ethyl acetate, the combined organic layers were washed with brine, dried (MgSO4) and concentrated under vacuum. The title compound (10 mg, 38%) was isolated by flash chromatography eluting with 50% acetone in methylene chloride. Mass spectrum: m/e 433 (M+1).

Workup

  1. customwas then quenched with saturated aqueous ammonium chloride solution
  2. extractionAfter extracting twice with ethyl acetate
  3. washthe combined organic layers were washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-fb96183b9ee54b9cadd4217196893d00
Source dataset
uspto-grants-2009_06
Patent number
US07553877B2

Reaction notes

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