Sodium Hydroxide → 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

HRID 1086542Notes

Reaction equation

HRID 1086542 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([O:28][C:29]([NH:31][C:32]2[CH:33]=[C:34]3[C:38](=[CH:39][CH:40]=2)[N:37]([CH3:41])[CH:36]=[C:35]3[CH2:42][C:43]2[CH:51]=[CH:50][C:46]([C:47]([OH:49])=[O:48])=[CH:45][C:44]=2[O:52][CH3:53])=[O:30])[CH2:27][CH2:26][CH2:25][CH2:24]1.[OH-:54].[Na+]>C(O)C>[C:17]1([N:8]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:13]([O:48][C:47](=[O:49])[C:46]2[CH:50]=[CH:51][C:43]([CH2:42][C:35]3[C:34]4[C:38](=[CH:39][CH:40]=[C:32]([NH:31][C:29]([O:28][CH:23]5[CH2:24][CH2:25][CH2:26][CH2:27]5)=[O:30])[CH:33]=4)[N:37]([CH3:41])[CH:36]=3)=[C:44]([O:52][CH3:53])[CH:45]=2)=[O:54])[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 112931194-((5-(((Cyclopentyloxy)carbonyl)amino)-1-methyl-1H-indol-3-yl)methyl)-3-methoxybenzoic acidHCID 86743328N,N-Diphenylcarbamoylpyridinium hydrochloride

Product 1

HCID 867433274-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N,N-Diphenylcarbamoylpyridinium hydrochloride (0.132 g.) was added to a stirred solution of 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic acid (obtained as described in Example 9) (0.15 g.) and sodium hydroxide (0.35 ml. of 1M aqueous solution) in absolute ethanol (6 ml.), under an atomosphere of nitrogen. The mixture was stirred for 15 minutes, and was then partitioned between ethyl acetate (50 ml.) and water (30 ml.). The organic layer was washed successively with 1M hydrochloric acid (20 ml.) and saturated brine (20 ml.), then dried (MgSO4), and evaporated to give 4-[5-(cyclopentyloxycarbonyl)amino-1-methylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride, as a white foam. This foam was dissolved in N,N-dimethylformamide (DMF) (3 ml.), and added to a stirred solution of the sodium salt of benzenesulphonamide (0.19 g.) in DMF (6 ml.), under an atmosphere of nitrogen. The mixture was stirred for 1 hour and then poured into 1M hydrochloric acid (40 ml.). The acid mixture was extracted with ethyl acetate (2×30 ml.). The combined extracts were dried (MgSO4) and evaporated. The yellow oil obtained was purified by the following successive procedures:

Workup

  1. customwas then partitioned between ethyl acetate (50 ml.) and water (30 ml.)
  2. washThe organic layer was washed successively with 1M hydrochloric acid (20 ml.) and saturated brine (20 ml.)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-40f8c6e617284117897c71c457693a0f
Source dataset
uspto-grants-1991_07
Patent number
US05030643

Reaction notes

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