Tetrahydrofuran → HCID 18761436, compound

HRID 431739Notes

Reaction equation

HRID 431739 reaction equation
C([O:4][CH2:5][CH2:6][C:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([NH:17][C:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[O:19])=[CH:9][C:8]=1[NH:28][C:29]([C:31]1[NH:32][C:33]2[C:38]([CH:39]=1)=[CH:37][C:36]([O:40][CH3:41])=[CH:35][CH:34]=2)=[O:30])(=O)C.O1CCCC1.C(=O)([O-])[O-].[K+].[K+]>CO.CCOC(C)=O>[CH2:21]([O:20][C:18]([NH:17][C:10]1[C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:7]([CH2:6][CH2:5][OH:4])=[C:8]([NH:28][C:29]([C:31]2[NH:32][C:33]3[C:38]([CH:39]=2)=[CH:37][C:36]([O:40][CH3:41])=[CH:35][CH:34]=3)=[O:30])[CH:9]=1)=[O:19])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 3

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 18761419HCID 18761419, compound

Product 1

HCID 18761436HCID 18761436, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-[4-(N-benzyloxycarbonylamino)-2-(5-methoxyindole-2-carboxamido)naphthalen-1-yl]ethyl acetate (0.5 g, 0.91 mmol) in methanol: tetrahydrofuran=1:1 (10 mL) was added potassium carbonate (0.13 g, 0.91 mmol) at room temperature and stirred overnight. The reaction mixture was diluted with AcOEt (100 mL) and washed with H2O (20 mL), saturated aqueous NaCl (20 mL), and then the organic layer was dried (Na2SO4) and concentrated under reduced pressure to yield as a brown foam 2-[4-(N-benzyloxycarbonylamino)-2-(5-methoxyindole-2-carboxamido)naphthalen-1-yl]ethanol (0.42 g, 94%): mp 198° C. (decomp.); 1H NMR (DMSO-d6, 500 MHz) δ 10.18 (s, 1H), 8.26 (d, 8.5, 1H), 7.97 (d, 8.5, 1H), 7.51 (t, 7.0, 1H), 7.43 (d, 8.5, 1H), 7.39 (d, 7.5, 2H), 7.33 (s, 1H), 7.31 (s, 1H), 7.28 (t, 7.5, 2H), 7.18 (t, 7.5, 1H), 7.11 (brs, 1H), 7.08 (d, 2.5, 1H), 6.91 (t, 6.0, 1H), 6.86 (dd, 9.0, 2.5, 1H), 6.81 (s, 1H), 5.35 (t, 4.5, 1H), 4.47 (d, 5.5, 2H), 3.76 (s, 3H), 3.69 (m, 2H), 3.11 (t, 6.0, 2H);); FABMS (NBA) m/z 465 (M−CO2+), IR (neat) νmax 3272, 2945, 2874, 1646, 1594, 1528, 1479, 1453, 1422, 1404, 1261, 1213, 1162, 1030, 841, 805, 758, 734, 699 cm−1.

Workup

  1. washwashed with H2O (20 mL), saturated aqueous NaCl (20 mL)
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-55c0f823a86c4814b9ea58c6f77ec312
Source dataset
uspto-grants-2003_12
Patent number
US06660742B2

Reaction notes

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