Acetic Acid → 5-[(R)-2-amino-1-(tert-butyldimethylsilyloxy)ethyl]-2-hydroxyphenylformamide acetate

HRID 2113257Notes

Reaction equation

HRID 2113257 reaction equation
C([NH:8][CH2:9][C@@H:10]([C:19]1[CH:20]=[CH:21][C:22]([O:28]CC2C=CC=CC=2)=[C:23]([NH:25][CH:26]=[O:27])[CH:24]=1)[O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])C1C=CC=CC=1.[C:36]([OH:39])(=[O:38])[CH3:37]>CO>[C:36]([OH:39])(=[O:38])[CH3:37].[NH2:8][CH2:9][C@@H:10]([C:19]1[CH:20]=[CH:21][C:22]([OH:28])=[C:23]([NH:25][CH:26]=[O:27])[CH:24]=1)[O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 57461066N-{5-[(R)-2-benzylamino-1-(tert-butyldimethylsilanyloxy)ethyl]-2-benzyloxyphenyl}formamide

Product 1

HCID 574610645-[(R)-2-amino-1-(tert-butyldimethylsilyloxy)ethyl]-2-hydroxyphenylformamide acetateYield 98%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Crude N-{5-[(R)-2-benzylamino-1-(tert-butyldimethylsilanyloxy)ethyl]-2-benzyloxyphenyl}formamide (100 g, 194 mmol) was dissolved in methanol (1 L) and acetic acid (25 mL, 291 mmol). The resulting mixture was purged with dry nitrogen and then palladium hydroxide on carbon (20 g, 20 wt. %, about 50% water) was added. Hydrogen was bubbled through the reaction mixture with stirring at room temperature for about 10 hours. The mixture was then purged with dry nitrogen and the mixture was filtered through Celite. The filtrate was concentrated on a rotary evaporator and ethyl acetate (600 mL) was added to the residue. This mixture was stirred for about 2 hours at which time a thick yellow slurry had developed. The slurry was filtered and the precipitate was air dried to provide N-{5-[(R)-2-amino-1-(tert-butyldimethylsilanyloxy)ethyl]-2-hydroxyphenyl}formamide acetic acid salt (48 g, 98% purity) as a yellow-white solid. LCMS (10-70) Rt=3.62; [M+H+] found 311.3.

Workup

  1. customThe resulting mixture was purged with dry nitrogen
  2. additionpalladium hydroxide on carbon (20 g, 20 wt. %, about 50% water) was added
  3. customHydrogen was bubbled through the reaction mixture
  4. customThe mixture was then purged with dry nitrogen
  5. filtrationthe mixture was filtered through Celite
  6. concentrationThe filtrate was concentrated on a rotary evaporator and ethyl acetate (600 mL)
  7. additionwas added to the residue
  8. stirringThis mixture was stirred for about 2 hours at which time a thick yellow slurry
  9. filtrationThe slurry was filtered
  10. customdried

Sources & evidence

ORD record
ord-a1beee76a7554a80ba567a44b7defc20
Source dataset
uspto-grants-2009_04
Patent number
US07524965B2

Reaction notes

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