Water → HCID 86602730, compound

HRID 1244821Notes

Reaction equation

HRID 1244821 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][CH2:5][C:6]#[C:7][C:8]([NH2:11])([CH3:10])[CH3:9].C(N(CC)CC)C.[Br:19][CH:20]([CH2:24][CH3:25])[C:21](Br)=[O:22].O>ClCCl>[Br:19][CH:20]([CH2:24][CH3:25])[C:21]([NH:11][C:8]([CH3:10])([CH3:9])[C:7]#[C:6][CH2:5][CH2:4][CH2:3][Cl:2])=[O:22]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 1172932-Bromobutanoyl bromideHCID 86602731HCID 86602731, compound

Product 1

HCID 86602730HCID 86602730, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

The product from Step 2 (12.2 g) was suspended in dry dichloromethane (300 ml), cooled to 5° C. with stirring and dry triethylamine (18.1 ml) was added. The mixture was stirred for 0.25 hours and 2-bromobutyryl bromide (14.3 g) in dichloromethane (25 ml) was added dropwise over 0.5 hours at 10–18° C. The mixture was stirred for a further 0.5 hours then allowed to warm to ambient temperature for 2 hours and stored for 18 hours. Water was added and the organic phase was separated, washed with water (three times), dried over magnesium sulphate then evaporated under reduced pressure to give the required product as a dark yellow oil, 17.4 g, 1H NMR (CDCl3) δ: 1.04(3H, t); 1.62(6H, s); 1.96(2H, m); 2.10(2H, m); 2.38(2H, m); 3.66(2H, t); 4.12(1H, t); 6.44(1H, s).

Workup

  1. stirringThe mixture was stirred for 0.25 hours
  2. stirringThe mixture was stirred for a further 0.5 hours
  3. temperatureto warm to ambient temperature for 2 hours
  4. customthe organic phase was separated
  5. washwashed with water (three times)
  6. dry with materialdried over magnesium sulphate
  7. customthen evaporated under reduced pressure

Sources & evidence

ORD record
ord-010885194af44b95979420a08d126978
Source dataset
uspto-grants-2006_10
Patent number
US07122672B2

Reaction notes

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