Hydrochloric Acid → HCID 89518063, compound

HRID 571222Notes

Reaction equation

HRID 571222 reaction equation
[C:1]([O:5][C:6]([N:8]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][C:23]([O:25]CC)=[O:24])[CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>C1COCC1.O.C(OCC)(=O)C>[C:1]([O:5][C:6]([N:8]([C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([CH2:22][C:23]([OH:25])=[O:24])[CH:14]=1)[S:9]([CH3:12])(=[O:11])=[O:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 86681639HCID 86681639, compound

Product 1

HCID 89518063HCID 89518063, compoundYield 95.4%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 21881883Oxolane--water (1/1)Solvent

Procedure

A suspension of ethyl 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-1H-indol-1-yl)acetate (248 mg, 0.626 mmol) and LiOH (74.9 mg, 3.13 mmol) in THF/water 1/1 (10 ml) was stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate and carefully acidified by slow addition of 1N HCl (pH=1). The phases were separated and the aqueous layer was extracted with ethyl acetate; the combined organic layers were dried over Na2SO4 and evaporated to dryness to give 2-(3-(N-(tert-butoxycarbonyl)methylsulfonamido)-1H-indol-1-yl)acetic acid as a yellow solid (220 mg, 0.597 mmol, 95% yield). MS/ESI+ 369.1 [MH]+.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous layer was extracted with ethyl acetate
  3. dry with materialthe combined organic layers were dried over Na2SO4
  4. customevaporated to dryness

Sources & evidence

ORD record
ord-1a45a59251ac4f99a826399721069db3
Source dataset
uspto-grants-2015_05
Patent number
US09024027B2

Reaction notes

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