Sodium Hydroxide → 1-[2-[[(1,1-Dimethylethoxy)carbonyl]amino]ethyl]-1H-indole-6-carboxylic acid

HRID 1478861Notes

Reaction equation

HRID 1478861 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1[CH:15]=[C:14]2[C:10]([CH:11]=[CH:12][N:13]2[CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:9][CH:8]=1)=[O:6]>CO.C1COCC1>[C:22]([O:21][C:19]([NH:18][CH2:17][CH2:16][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[C:7]([C:5]([OH:6])=[O:4])[CH:15]=2)[CH:11]=[CH:12]1)=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86725264HCID 86725264, compound

Product 1

HCID 247209431-[2-[[(1,1-Dimethylethoxy)carbonyl]amino]ethyl]-1H-indole-6-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydroxide (1N, 6.0 mL, 6.00 mmol) was added to a solution of 1-(2-tert-Butoxycarbonylamino-ethyl)-1H-indole-6-carboxylic acid methyl ester (0.501 g, 1.57 mmol) in methanol (12 mL) and THF (4.0 mL). The reaction was stirred at room temperature for 68 hr. The reaction was concentrated in vacuo. The aqueous residue was acidified to pH˜1 with 1N HCl and extracted with ethyl acetate (3×). The combined organic layers were dried over Na2SO4, filtered, and concentrated. The crude product was carried forward without purification. ESI-MS m/z 327 (M+Na).

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. extractionextracted with ethyl acetate (3×)
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was carried forward without purification

Sources & evidence

ORD record
ord-cd9cee708a1a46be81c074628b3f9aaf
Source dataset
uspto-grants-2016_08
Patent number
US09403850B2

Reaction notes

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