Benzyl 8-bromooctanoate → 7-(benzyloxycarbonyl)heptyl 5-(Cbz-amino)-4-oxopentanoate

HRID 1771047

Reaction equation

HRID 1771047 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10].[C:19]([NH:29][CH2:30][C:31](=[O:37])[CH2:32][CH2:33][C:34]([O-:36])=[O:35])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20].[Cs+]>>[C:19]([NH:29][CH2:30][C:31](=[O:37])[CH2:32][CH2:33][C:34]([O:36][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:10])=[O:35])([O:21][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20]

Participants

3

Reactant 2

HCID 11278409Benzyl 8-bromooctanoateHCID 90034572caesium 5-(Cbz-amino)-4-oxopentanoate

Product 1

HCID 900344997-(benzyloxycarbonyl)heptyl 5-(Cbz-amino)-4-oxopentanoate

Procedure

This compound was prepared from the product of 10a (0.79 g; 2.5 mmol) and 8b (1.0 g; 2.5 mmol) according to Procedure C. The reaction time was 2 days. The crude product was purified on a 80×45 mm silica gel 60 column eluted with ethyl acetate-hexane (1:1) (1000 mL) collecting 13×50 mL fractions. Fractions containing the product (3-6) were collected, and after evaporation 0.83 g (67%) product was obtained (amber oil that solidified to a waxy solid on standing in the freezer, mp 52-54° C.).

Workup

  1. customThe crude product was purified on a 80×45 mm silica gel 60 column
  2. washeluted with ethyl acetate-hexane (1:1) (1000 mL)
  3. customcollecting 13×50 mL fractions
  4. additionFractions containing the product (3-6)
  5. customwere collected
  6. customafter evaporation 0.83 g (67%) product
  7. customwas obtained (amber oil that

Sources & evidence

ORD record
ord-0d90948317b841739fc4c1030ed85373
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Linked notes

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