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

HRID 267076Notes

Reaction equation

HRID 267076 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 esterYield 167.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

N-[2(S)-(t-Butoxycarbonylamino)-3(S)-methyl-pentyl]glycine methyl ester (6, 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 triacetoxy-borohydride (6.65 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 7.

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

Sources & evidence

ORD record
ord-315141eedbf84de3b91220ac86fd42e2
Source dataset
uspto-grants-1997_07
Patent number
US05652257

Reaction notes

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