1-Naphthaldehyde → N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester

HRID 1741478Notes

Reaction equation

HRID 1741478 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH2:4][NH:5][CH2:6][C@@H:7]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C@@H:8]([CH3:11])[CH2:9][CH3:10].[C:21]1([CH:31]=O)[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:1][O:2][C:3](=[O:20])[CH2:4][N:5]([CH2:6][C@@H:7]([NH:12][C:13]([O:15][C:16]([CH3:18])([CH3:17])[CH3:19])=[O:14])[C@@H:8]([CH3:11])[CH2:9][CH3:10])[CH2:31][C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 61951-NaphthaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 10755806N-(2(S)-(t-butoxycarbonylamino)-3(S)-methylpentyl)glycine methyl ester

Product 1

HCID 10526565N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]-N-(1-naphthylmethyl)glycine methyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methylpentyl]glycine methyl ester (2.00 g, 6.97 mmol) was dissolved in 1,2-dichloroethane (56 ml) and 3A molecular sieves were added followed by 1-naphthaldehyde (1.89 ml, 13.9 mmol) and sodium triacetoxyborohydride (6.65 g, 31.4 mmol). The mixture was stirred at ambient temperature for 16 h, filtered and evaporated in vacuo. The residue was partitioned between EtOAc (100 ml) and sat. aq. NaHCO3 (25 ml). The aqueous layer was extracted with EtOAc (3×50 ml). The organic extracts were combined, dried (Na2SO4), filtered, and evaporated in vacuo to afford a residue which was purified by chromatography (SiO2, 15-33% ethyl acetate in hexanes) to afford the title compound as an oil.

Workup

  1. filtrationfiltered
  2. customevaporated in vacuo
  3. customThe residue was partitioned between EtOAc (100 ml) and sat. aq. NaHCO3 (25 ml)
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customto afford a residue which
  9. customwas purified by chromatography (SiO2, 15-33% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-4461482d6bd44a30a40774bb54a0b729
Source dataset
uspto-grants-1999_10
Patent number
US05972984

Reaction notes

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