Hydrochloric Acid → HCID 90460801, compound

HRID 625877Notes

Reaction equation

HRID 625877 reaction equation
O.[OH-].[Li+].[C:4]([O:8][C:9](=[O:34])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C@H:21]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:22]([O:24]C)=[O:23])=[CH:12]1)([CH3:7])([CH3:6])[CH3:5].Cl>O1CCOCC1.O>[C:4]([O:8][C:9](=[O:34])[CH2:10][N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][C@H:21]([NH:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:22]([OH:24])=[O:23])=[CH:12]1)([CH3:6])([CH3:7])[CH3:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 90461420HCID 90461420, compound

Product 1

HCID 90460801HCID 90460801, compoundYield 78%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydrate (0.455 g, 10.84 mmol) was added to a solution of (S)-methyl 3-(1-(2-(tert-butoxy)-2-oxoethyl)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoate (4.69 g, 10.84 mmol) in dioxane (50 mL) and water (16.67 mL) and stirred at RT for 1 hr. The reaction was neutralized with 1M HCl and extracted with EtOAc. The organic layer washed with brine, collected, dried over MgSO4, filtered and evaporated to give the crude material. The crude material was purified via silica gel chromatography (120 g column, 0-50% EtOAc:Hex over 20 CV) to get the product (S)-3-(1-(2-(tert-butoxy)-2-oxoethyl)-1H-indol-3-yl)-2-((tert-butoxycarbonyl)amino)propanoic acid (3.54 g, 78% yield). 1H NMR (400 MHz, chloroform-d) d 7.62 (d, J=7.8 Hz, 1H), 7.26-7.21 (m, 2H), 7.15 (ddd, J=7.9, 5.6, 2.3 Hz, 1H), 6.99 (s, 1H), 5.08 (d, J=7.8 Hz, 1H), 4.71 (s, 2H), 4.65 (br. s., 1H), 3.42-3.31 (m, 2H), 1.46 (s, 18H). ESI-MS(+) m/z=441 (M+Na).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic layer washed with brine
  3. customcollected
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customto give the crude material
  8. customThe crude material was purified via silica gel chromatography (120 g column, 0-50% EtOAc:Hex over 20 CV)

Sources & evidence

ORD record
ord-9710ec878b744871bcae42948695ca0f
Source dataset
uspto-grants-2016_04
Patent number
US09308236B2

Reaction notes

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