Triethylamine → HCID 90034562, compound

HRID 1771032Notes

Reaction equation

HRID 1771032 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[C:15]([NH:22][CH2:23][C:24](=[O:30])[CH2:25][CH2:26][C:27]([O-:29])=[O:28])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16].C(N(CC)CC)C>C(OCC)(=O)C>[C:15]([NH:22][CH2:23][C:24](=[O:30])[CH2:25][CH2:26][C:27]([O:29][CH2:2][CH2:3][CH2:4][C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6])=[O:28])([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 3832489Benzyl 4-bromobutanoateHCID 131734642HCID 131734642, compound

Product 1

HCID 90034562HCID 90034562, compoundYield 47.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

This compound was prepared from benzyl 4-bromobutanoate (7.2 g; 28.0 mmol), 5-(Boc-amino)-4-oxopentanoate (6.7 g; 29.0 mmol), triethylamine (2.95 mmol), and ethyl acetate (100 mL) as described in Example 1a. The crude product was purified by flash chromatography on a 60×55 mm silica gel 60 column eluted with ethyl acetate-hexane (1:2) (750 mL) collecting 6×100 mL fractions. After evaporation of fractions 3 and 4, 5.43 g (46%) product was obtained (yellow oil).

Workup

  1. customThe crude product was purified by flash chromatography on a 60×55 mm silica gel 60 column
  2. washeluted with ethyl acetate-hexane (1:2) (750 mL)
  3. customcollecting 6×100 mL fractions
  4. customAfter evaporation of fractions 3 and 4

Sources & evidence

ORD record
ord-c8c4bb36d6ad4652afea1a12e397845d
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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