Hydrochloric Acid → 12-(2-Iodoacetylamino)dodecanoic acid 2,5-dioxopyrrolidin-1-yl ester

HRID 593236Notes

Reaction equation

HRID 593236 reaction equation
[I:1][CH2:2][C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:4].[B-](F)(F)(F)F.CN(C(O[N:33]1[C:38](=[O:39])[CH2:37][CH2:36][C:34]1=[O:35])=[N+](C)C)C.CCN(C(C)C)C(C)C.Cl>C1COCC1>[O:35]=[C:34]1[CH2:36][CH2:37][C:38](=[O:39])[N:33]1[O:18][C:17](=[O:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:3](=[O:4])[CH2:2][I:1]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 81531DiisopropylethylamineHCID 98575222-(2,5-Dioxopyrrolidin-1-yl)-1,1,3,3-tetramethylisouronium tetrafluoroborateHCID 5085270012-(2-Iodoacetylamino)dodecanoic acid

Product 1

HCID 8665101612-(2-Iodoacetylamino)dodecanoic acid 2,5-dioxopyrrolidin-1-yl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 12-(2-Iodoacetylamino)dodecanoic acid (460 mg) in THF (10 ml) was added TSTU (415 mg) and DIPEA (0.315 ml). After stirring at room temperature for 2 h, the mixture was pored in to 0.5 N HCl (200 ml) and was extracted with ethyl acetate (2×200 ml). The combined organic layers was washed with 0.1 N HCl and brine, dried with magnesium sulphate and concentrated. The residue was used without further purification. Yield, 99% (575 mg). LC-MS, M/z: 481.2 (M+1).

Workup

  1. extractionwas extracted with ethyl acetate (2×200 ml)
  2. washThe combined organic layers was washed with 0.1 N HCl and brine
  3. dry with materialdried with magnesium sulphate
  4. concentrationconcentrated
  5. customThe residue was used without further purification
  6. customYield

Sources & evidence

ORD record
ord-9fd30999f3d64c2daf07fd50291abba7
Source dataset
uspto-grants-2016_01
Patent number
US09242011B2

Reaction notes

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