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

HRID 259967Notes

Reaction equation

HRID 259967 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 (665 g, 31.4 mmol). The mixture was stirred at ambient temperature for 16 h, and filtered through glass fiber paper and concentrated. The residue was partitioned between EtOAc and sat. NaHCO3 (100 ml/25 ml). The aqueous layer was extracted with EtOAc (3×50 ml). The organic layers were combined, dried (Na2SO4), filtered, and Concentrated to give 5.0 g of crude product which was purified by chromatography (SiO2, 15-33% ethyl acetate/hexane) to give the title compound.

Workup

  1. filtrationfiltered through glass fiber paper
  2. concentrationconcentrated
  3. customThe residue was partitioned between EtOAc and sat. NaHCO3 (100 ml/25 ml)
  4. extractionThe aqueous layer was extracted with EtOAc (3×50 ml)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationConcentrated
  8. customto give 5.0 g of crude product which
  9. customwas purified by chromatography (SiO2, 15-33% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-39281dd44897474a9df24c3d16165f1a
Source dataset
uspto-grants-1996_06
Patent number
US05523456

Reaction notes

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