Acetic Acid → HCID 59687917, compound

HRID 444999Notes

Reaction equation

HRID 444999 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5].[C:7]([O:11][C:12](=[O:32])[CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH:21]=O)[CH:18]=[C:17]([O:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:16]=1)([CH3:10])([CH3:9])[CH3:8].C([BH3-])#N.[Na+].C(O)(=O)C>CO.O>[C:7]([O:11][C:12]([CH2:13][O:14][C:15]1[CH:20]=[C:19]([CH:18]=[C:17]([O:23][CH2:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH:16]=1)[CH2:21][NH:1][CH2:2][CH2:3][C:4]([OH:6])=[O:5])=[O:32])([CH3:9])([CH3:10])[CH3:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 239Beta-AlanineHCID 5003444Sodium cyanoborohydrideHCID 58079465(3-Tert-Butoxycarbonylmethoxy-5-formylphenoxy)acetic acid tert-butyl ester

Product 1

HCID 59687917HCID 59687917, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

Beta-alanine (0.5 g, 5.68 mmol) was dissolved in methanol (20 mL). (3-Tert-Butoxycarbonylmethoxy-5-formylphenoxy)acetic acid tert-butyl ester (2.08 g, 5.58 mmol) was dissolved in methanol (2 mL) and added. The mixture was heated to reflux for 1 hour and allowed to cool to room temperature. Sodium cyanoborohydride (282 mg, 4.54 mmol) was added and the mixture stirred at room temperature, after 1 hour acetic acid was added (2 mL) and the mixture was stirred for an additional hour before being poured into water (50 mL) and stirred overnight. The water phase was washed with ethyl acetate (2×50 mL). The organic phase was dried (Na2SO4) and solvent removed in vacuo to yield the crude product. The crude product was used in the next step without further purification.

Workup

  1. additionadded
  2. temperatureThe mixture was heated
  3. temperatureto reflux for 1 hour
  4. additionwas added (2 mL)
  5. stirringstirred overnight
  6. washThe water phase was washed with ethyl acetate (2×50 mL)
  7. dry with materialThe organic phase was dried (Na2SO4) and solvent
  8. customremoved in vacuo

Sources & evidence

ORD record
ord-b67d1ff4bb914374b6091c234388c05a
Source dataset
uspto-grants-2013_07
Patent number
US08476228B2

Reaction notes

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