Ethyl Acetate → 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 1904468Notes

Reaction equation

HRID 1904468 reaction equation
[Cl-].[C:2]1([N+:8]2([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:13]=CC=CC2C(=O)N)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:23]1([CH2:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH2:41][CH3:42])[CH:36]=[C:35]3[CH2:43][C:44]2[CH:52]=[CH:51][C:47]([C:48]([OH:50])=[O:49])=[CH:46][C:45]=2[O:53][CH3:54])=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-].[Na+].C(OCC)(=[O:59])C>CO.CN(C)C=O>[C:17]1([N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]([O:49][C:48](=[O:50])[C:47]2[CH:51]=[CH:52][C:44]([CH2:43][C:35]3[C:34]4[C:38](=[CH:39][CH:40]=[C:32]([NH:31][C:29](=[O:30])[CH2:28][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)[CH:33]=4)[N:37]([CH2:41][CH3:42])[CH:36]=3)=[C:45]([O:53][CH3:54])[CH:46]=2)=[O:59])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

7

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 146268494-[5-(2-Cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic acidHCID 86743117N,N-diphenylcarbamoylpyridinium chloride

Product 1

HCID 867431194-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6228DimethylformamideSolvent

Procedure

A solution of N,N-diphenylcarbamoylpyridinium chloride (311 mg) in methanol (1 ml) was added to a stirred solution of the acid (J) (450 mg) and sodium hydroxide (1 ml of a 1M aqueous solution) in methanol (4 ml) under an atmosphere of nitrogen. After stirring for 1.5 minutes, ethyl acetate and N,N-dimethylformamide (2 ml) were added and the mixture allowed to stir until all dissolved. The ethyl acetate solution was washed with water and saturated brine, dried (MgSO4) and evaporated to give a quantitative yield of 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride (E) as a crusty foam; partial NMR: (80 MHz, DMSO-d6): 1.30(t, J=7.1 Hz, 2H, NCH2CH3), 3.84(s, 3H, OCH3), 3.94(s, 2H, ArCH2), 4.05(q, J=7.1 Hz, 2H, NCH2CH3), 7.41(s, 10H, NArH), 9.56(s, 1H, CONH).

Workup

  1. stirringto stir until all dissolved
  2. washThe ethyl acetate solution was washed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-1d1426579a924c6e9b608c04d3fd6f32
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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