Sodium Hydroxide → 4-(3-(3-(Tert-butoxycarbonylamino)-1-hydroxypropyl)phenoxy)butanoic acid

HRID 74403Notes

Reaction equation

HRID 74403 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=1)[O:16][CH2:17][CH2:18][CH2:19][C:20]([O:22]CC)=[O:21])[OH:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C1COCC1.CO>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH:11]([C:13]1[CH:14]=[C:15]([CH:25]=[CH:26][CH:27]=1)[O:16][CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[OH:12])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 67317450HCID 67317450, compound

Product 1

HCID 673166134-(3-(3-(Tert-butoxycarbonylamino)-1-hydroxypropyl)phenoxy)butanoic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To the ester 130 (2.3 g, 6.0 mmol) in THF (80 mL) and MeOH (20 mL) was added NaOH solution (8 mL, 2N). The resulting mixture was stirred at room temperature for overnight following which the solvent was removed under reduced pressure and pH adjusted to 6 by the addition of cold dilute HCl. This was then extracted with DCM. The organic layer was washed with water, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to give 4-(3-(3-(tert-butoxycarbonylamino)-1-hydroxypropyl)phenoxy)butanoic acid (131). The product was directly utilized for the next transformation. Yield (1.94 g, 91%): 1H NMR (400 MHz, CDCl3) δ 7.18-7.22 (m, 1H), 6.84-6.90 (m, 2H), 6.77 (dd, J=7.6, 1.6 Hz, 1H), 5.18 (bs, 1H), 4.48-4.53 (m, 1H), 3.96 (t, J=6.4 Hz, 2H), 2.93-2.99 (m, 2H), 2.38 (t, J=7.4 Hz, 2H), 1.90-1.96 (m, 2H), 1.64-1.71 (m, 2H), 1.45 (s, 9H).

Workup

  1. customwas removed under reduced pressure
  2. additionpH adjusted to 6 by the addition of cold dilute HCl
  3. extractionThis was then extracted with DCM
  4. washThe organic layer was washed with water
  5. dry with materialdried over anhydrous Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8b201db9f88c4559a7fb7be98c6068ca
Source dataset
uspto-grants-2014_09
Patent number
US08829244B2

Reaction notes

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