Benzyl 5-bromopentanoate → HCID 90034571, compound

HRID 1771041Notes

Reaction equation

HRID 1771041 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[C:16]([NH:26][CH2:27][C:28](=[O:34])[CH2:29][CH2:30][C:31]([O-:33])=[O:32])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].[Cs+]>>[C:16]([NH:26][CH2:27][C:28](=[O:34])[CH2:29][CH2:30][C:31]([O:33][CH2:2][CH2:3][CH2:4][CH2:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])=[O:32])([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

Participants

3

Reactant 2

HCID 562251Benzyl 5-bromopentanoateHCID 90034572caesium 5-(Cbz-amino)-4-oxopentanoate

Product 1

HCID 90034571HCID 90034571, compound

Procedure

This compound was prepared from the products of 8a (0.73 g; 2.7 mmol) and 8b (1.0 g; 2.5 mmol) according to Procedure C. The crude product was purified on a 75×45 mm silica gel 60 column eluted with ethyl acetate-hexane (1:1) (1000 mL) collecting 13×50 mL fractions. Fractions containing the product (5-8) were collected, and after evaporation 0.82 g (72%) product was obtained (yellowish solid, mp 53-56° C.).

Workup

  1. customThe crude product was purified on a 75×45 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 (5-8)
  5. customwere collected
  6. customafter evaporation 0.82 g (72%) product
  7. customwas obtained (yellowish solid, mp 53-56° C.)

Sources & evidence

ORD record
ord-2ad0d7b34f2c4dff974eeb7e5345eb9e
Source dataset
uspto-grants-2016_02
Patent number
US09249086B2

Reaction notes

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