Bromoacetyl bromide → HCID 86666541, compound

HRID 1397128Notes

Reaction equation

HRID 1397128 reaction equation
[CH2:1]([O:4][C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][NH2:12])=[O:6])[CH:2]=[CH2:3].CN(C1C2C(N(C)C)=CC=CC=2C=CC=1)C.[Br:29][CH2:30][C:31](Br)=[O:32]>ClCCl>[Br:29][CH2:30][C:31]([NH:12][CH2:11][CH2:10][CH2:9][CH2:8][NH:7][C:5](=[O:6])[O:4][CH2:1][CH:2]=[CH2:3])=[O:32]

Participants

5

Reactant 3

HCID 61147Bromoacetyl bromideHCID 88675Proton spongeHCID 16211079HCID 16211079, compound

Product 1

HCID 86666541HCID 86666541, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4-((Allyloxycarbonyl)amino)butan-1-amine (87c, 1.18 g, 6.852 mmol, prepared according to Synthesis, 2002, 15, 2195) and proton sponge (1.468 g, 6.850 mmol) were dissolved in 14 mL of dichloromethane followed by the dropwise addition of 0.6 mL (6.908 mmol) of bromoacetyl bromide. After overnight stirring at room temperature, the mixture was diluted with dichloromethane, washed with water (2×) and brine (1×) and dried over sodium sulfate. The concentrated crude material was subjected to a Biotage™ flash chromatography system on a silica gel column with 40:1 (v/v) dichloromethane/methanol as the eluent. Product 88c (1.52 g, 76% yield) was obtained as an off-white solid. 1H NMR (400 MHz, CDCl3) δ 1.69 (m, 4H), 3.22 (q, J=6.2, 2H), 3.32 (q, J=6.2, 2H), 3.88 (s, 2H), 4.56 (d, J=5.1, 2H), 4.80 (broad s, 1H), 5.21 (dd, J=1.1, 10.6, 1H), 5.30 (dd, J=1.8, 17.2, 1H), 5.92 (octet, J=5.6 Hz, 1H), 6.58 (broad s, 1H).

Workup

  1. washwashed with water (2×) and brine (1×)
  2. dry with materialdried over sodium sulfate
  3. concentrationThe concentrated crude material

Sources & evidence

ORD record
ord-3b0d3b68a6fb418cbd48b8c6ce9ff048
Source dataset
uspto-grants-2014_12
Patent number
US08901072B2

Reaction notes

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