Methanol → HCID 86685804, compound

HRID 2361590Notes

Reaction equation

HRID 2361590 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:15]([CH3:23])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:22])[CH:20]=[CH2:21])[C:10]([O:12]CC)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO.[Li+].[OH-]>C1COCC1.O>[C:1]([O:5][C:6]([NH:8][CH:9]([C@H:15]([CH3:23])[CH2:16][CH2:17][CH2:18][CH:19]([CH3:22])[CH:20]=[CH2:21])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 887MethanolHCID 3939Lithium HydroxideHCID 86685803HCID 86685803, compound

Product 1

HCID 86685804HCID 86685804, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of (3R)-ethyl 2-(tert-butoxycarbonylamino)-3,7-dimethylnon-8-enoate (2.7 g, 8.25 mmol) in THF/water (40 mL, 1:1) was added methanol (20 mL) followed by LiOH (0.987 g, 41.2 mmole) at room temperature. The reaction mass was stirred at room temperature overnight. Solvent was evaporated under reduced pressure and the residue was diluted with water (100 mL). The aqueous solution was acidified with aqueous 1.5 N HCl solutions to pH˜3 and extracted with ethyl acetate (100 mL×3). The combined organic layer was dried over anhydrous Na2SO4 and concentrated under reduce pressure to get crude compound. The crude compound was purified by column chromotography (Silica gel, 3% methanol in DCM) to get 2.1 g (85%) of desired compound as gummy liquid. 1H NMR (400 MHz, DMSO-D6): δ ppm 12.2-12.02 (bs, 1H), 6.92-6.85 (m, 1H) 5.72-5.66 (m, 1H), 4.98-4.85 (dd, J=1.6, 2.8 Hz, 2H), 4.03-3.95 (m, 1H), 2.58-2.56 (m, 1H) 2.15-2.02 (m, 1H), 1.45-1.36 (m, 10H), 1.27-1.21 (m, 5H), 0.95-0.93 (m, 3H), 0.84-0.74 (m, 3H).

Workup

  1. customSolvent was evaporated under reduced pressure
  2. additionthe residue was diluted with water (100 mL)
  3. extractionextracted with ethyl acetate (100 mL×3)
  4. dry with materialThe combined organic layer was dried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customto get crude compound
  7. customThe crude compound was purified by column chromotography (Silica gel, 3% methanol in DCM)

Sources & evidence

ORD record
ord-cb2e197b976d4d13bc6939601665d80f
Source dataset
uspto-grants-2014_04
Patent number
US08691757B2

Reaction notes

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