Hydrochloric Acid → HCID 58172052, compound

HRID 560171Notes

Reaction equation

HRID 560171 reaction equation
C([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=[CH:12][C:11]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[CH:10][CH:9]=2)=[O:5])C.O.[OH-].[Li+].Cl>C(O)C.O>[CH2:27]([O:26][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:4]([OH:5])=[O:3])=[C:14]2[CH2:15][CH2:16][CH2:17][NH:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 58172045HCID 58172045, compound

Product 1

HCID 58172052HCID 58172052, compoundYield 99.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

The above 5-benzyloxy-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid ethyl ester (0.2 g, 0.44 mmol, 1.0 equiv) was dissolved in 5 mL of ethanol. A solution of lithium hydroxide hydrate (0.2 g) in 5 mL of water was added and the resulting solution was stirred for 16 h at ambient temperature. The pH was adjusted to <1 with concentrated HCl and the product was quickly extracted with 2×15 mL of ethyl acetate. The organic layers were combined, dried over Na2SO4, decanted and concentrated to provide 5-benzyloxy-3-[3-(t-butoxycarbonylamino)-propyl]-1H-indole-2-carboxylic acid (186 mg) as a beige glass.

Workup

  1. extractionthe product was quickly extracted with 2×15 mL of ethyl acetate
  2. dry with materialdried over Na2SO4
  3. customdecanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-be31652d39d74930b651dd530489184a
Source dataset
uspto-grants-2011_11
Patent number
US08063094B2

Reaction notes

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