Lithium hydroxide, monohydrate → (2S)-2-[(tert-Butoxycarbonyl)amino]-8-oxononanoic acid

HRID 251721Notes

Reaction equation

HRID 251721 reaction equation
C[O:2][C:3](=[O:21])[C@@H:4]([NH:13][C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:12])[CH3:11].O[Li].O>C1COCC1.O>[C:17]([O:16][C:14]([NH:13][C@@H:4]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10](=[O:12])[CH3:11])[C:3]([OH:21])=[O:2])=[O:15])([CH3:20])([CH3:19])[CH3:18]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86627947(2S)-2-[(tert-Butoxycarbonyl)amino]-8-oxononanoic acid methyl ester

Product 1

HCID 86627946(2S)-2-[(tert-Butoxycarbonyl)amino]-8-oxononanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

(2S)-2-[(tert-Butoxycarbonyl)amino]-8-oxononanoic acid methyl ester (1 eq.) was dissolved in a 1:1 mixture of THF and water at RT and LiOH hydrate (1.2 eq.) was added and the mixture was stirred for 30 min. The mixture was partitioned between 0.1M HCl and DCM, separated and the organic phase was washed with water, dried (Na2SO4) and concentrated under reduced pressure. The colourless oil A1 obtained was used in the next step without purification. MS (ES) C14H25NO5 requires: 287, found: 288 (M+H)+.

Workup

  1. customThe mixture was partitioned between 0.1M HCl and DCM
  2. customseparated
  3. washthe organic phase was washed with water
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b7e33ada867245faa4f57e92df6a4b96
Source dataset
uspto-grants-2011_01
Patent number
US07863294B2

Reaction notes

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