Triethylamine → t-butyl alpha-[5-(Boc-amino)-4-oxopentanoyloxy]-phenylacetate

HRID 1771036Notes

Reaction equation

HRID 1771036 reaction equation
[C:1]([NH:8][CH2:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([OH:15])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].Br[CH:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(N(CC)CC)C>C(OCC)(=O)C>[C:1]([NH:8][CH2:9][C:10](=[O:16])[CH2:11][CH2:12][C:13]([O:15][CH:18]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:19]([O:21][C:22]([CH3:25])([CH3:23])[CH3:24])=[O:20])=[O:14])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11000147Tert-butyl 2-bromo-2-phenylacetateHCID 179898205-((tert-Butoxycarbonyl)amino)-4-oxopentanoic acid

Product 1

HCID 90034569t-butyl alpha-[5-(Boc-amino)-4-oxopentanoyloxy]-phenylacetateYield 78%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared from 5-(Boc-amino)-4-oxopentanoic acid (1.97 g; 8.5 mmol), the product of 6a (2.35 g; 8.7 mmol), and triethylamine (0.88 g; 8.7 mmol) in ethyl acetate (30 mL) as described in Example 1a. The crude product was purified by flash chromatography on a 65×55 mm silica gel 60 column eluted with ethyl acetate-hexane (1:2) (1100 mL) collecting 18×50 mL fractions. After evaporation of fractions 3-8, 2.79 g (78%) product was obtained (amber oil).

Workup

  1. customThe crude product was purified by flash chromatography on a 65×55 mm silica gel 60 column
  2. washeluted with ethyl acetate-hexane (1:2) (1100 mL)
  3. customcollecting 18×50 mL fractions
  4. customAfter evaporation of fractions 3-8

Sources & evidence

ORD record
ord-04cef073c8344c4382c5d0542e83d501
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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