Benzyl bromoacetate → HCID 90001511, compound

HRID 2200831Notes

Reaction equation

HRID 2200831 reaction equation
CCN(C(C)C)C(C)C.[OH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][NH:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:28])([CH3:27])[CH3:26].C(C(Br)C([O-])=O)C1C=CC=CC=1.Br[CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45]>C(#N)C.O>[OH:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][N:16]([CH2:43][C:44]([O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)=[O:45])[CH2:17][CH2:18][O:19][CH2:20][CH2:21][NH:22][C:23](=[O:29])[O:24][C:25]([CH3:26])([CH3:28])[CH3:27]

Participants

7

Reactant 4

HCID 62576Benzyl bromoacetateHCID 81531DiisopropylethylamineHCID 21881508BenzylbromoacetateHCID 123226547HCID 123226547, compound

Product 1

HCID 90001511HCID 90001511, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

DIPEA (0.23 mL, 2.0 eq.) was added to a solution of 18 (0.19 g, 1.0 eq.) in dry acetonitrile (1.5 mL) at 0° C. Benzylbromoacetate (0.11 mL, 1.0 eq.) was added in one portion and the reaction was allowed to warm to room temperature and stir for 18 hrs. A further portion of benzyl bromoacetate (55 μL) was added and the reaction was stirred for a further 2 h. The reaction was diluted with water (20 mL) and extracted into ethyl acetate (3×20 mL). The combined organic phases were washed with water (50 mL) and brine (50 mL) before being dried (MgSO4), filtered and concentrated at reduced pressure to yield give a colourless oil (0.40 g). The crude product was purified by silica column chromatography eluting with 3% methanolic ammonia in DCM to give 0.23 g (79%) of 19 as a colourless oil. 13C NMR (CDCl3) δ 171.3, 156.2, 135.7, 128.6, 128.4, 79.0, 72.3, 70.2, 69.4, 69.2, 66.2, 61.9, 55.2, 54.2, 40.5, 28.5. ESMS (C22H36N2O7) [M+H]+ calc. 441.2601. found 441.2596.

Workup

  1. stirringthe reaction was stirred for a further 2 h
  2. extractionextracted into ethyl acetate (3×20 mL)
  3. washThe combined organic phases were washed with water (50 mL) and brine (50 mL)
  4. dry with materialbefore being dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated at reduced pressure
  7. customto yield

Sources & evidence

ORD record
ord-3029e5ecf72b463aaa3196185085cfde
Source dataset
uspto-grants-2016_06
Patent number
US09359392B2

Reaction notes

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