Hydrochloric Acid → Methyl 2-[4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoyl]-2-phenylsulfonylacetate

HRID 1904463Notes

Reaction equation

HRID 1904463 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:11]1([S:17]([CH2:20][C:21]([O:23][CH3:24])=[O:22])(=[O:19])=[O:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N(C2C=CC=CC=2)C([O:34][C:35](=O)[C:36]2[CH:41]=[CH:40][C:39]([CH2:42][C:43]3[C:51]4[C:46](=[CH:47][CH:48]=[C:49]([NH:52][C:53](=[O:60])[CH2:54][CH:55]5[CH2:59][CH2:58][CH2:57][CH2:56]5)[CH:50]=4)[N:45]([CH2:61][CH3:62])[CH:44]=3)=[C:38]([O:63][CH3:64])[CH:37]=2)=O)C=CC=CC=1.P([O-])(O)(O)=O.[K+].Cl>C1(C)C=CC=CC=1.O1CCCC1>[CH:55]1([CH2:54][C:53]([NH:52][C:49]2[CH:50]=[C:51]3[C:46](=[CH:47][CH:48]=2)[N:45]([CH2:61][CH3:62])[CH:44]=[C:43]3[CH2:42][C:39]2[CH:40]=[CH:41][C:36]([C:35]([CH:20]([S:17]([C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=3)(=[O:19])=[O:18])[C:21]([O:23][CH3:24])=[O:22])=[O:34])=[CH:37][C:38]=2[O:63][CH3:64])=[O:60])[CH2:59][CH2:58][CH2:57][CH2:56]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 516951Monobasic potassium phosphateHCID 555619Methyl phenylsulfonyl acetateHCID 3251421Potassium bis(trimethylsilyl)amideHCID 86743119HCID 86743119, compound

Product 1

HCID 20038739Methyl 2-[4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoyl]-2-phenylsulfonylacetate

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of potassium bis(trimethylsilyl)amide (7.1 ml of a 0.8M solution in toluene) was added to a solution of methyl 2-(phenylsulfonyl)acetate (1.24 g) in tetrahydrofuran (THF) (9.0 ml) at -78° C. This mixture was then added to a solution of 4-[5-(2-cyclopentylacetamido)-1-ethylindol-3-ylmethyl]-3-methoxybenzoic N,N-diphenylcarbamic anhydride (E) (600 mg) in THF at -78° C. The reaction solution was allowed to warm to room temperature overnight and saturated potassium dihydrogen phosphate (20 ml) was then added. The mixture was made acidic to pH 4 with the addition of 1N HCl and partitioned with ethyl acetate. The organic layer was washed with water and saturated brine, dried (MgSO4) and evaporated. The residue was purified by chromatography on silica gel (41 g) using chloroform as the eluent. The title compound was obtained as an oil which was crystallized from methyl t-butyl ether/hexane to give a pale yellow solid (64.5 mg, 10%); mp 78°-80° C.

Workup

  1. custompartitioned with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customThe residue was purified by chromatography on silica gel (41 g)

Sources & evidence

ORD record
ord-5f3ff8440a39464bb4a820e3fa52b739
Source dataset
uspto-grants-1989_06
Patent number
US04837235

Reaction notes

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