Triethylamine → HCID 19048401, compound

HRID 233080Notes

Reaction equation

HRID 233080 reaction equation
[C:1]([O:4][CH:5]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([NH:17][C:18]([CH:20]2[CH2:24][CH2:23][CH2:22][O:21]2)=[O:19])[C:13]([I:25])=[C:12]([C:26]([NH:28][CH2:29][CH:30]([O:36][C:37](=[O:39])[CH3:38])[CH2:31][O:32][C:33](=[O:35])[CH3:34])=[O:27])[C:11]=1[I:40])=[O:9])(=[O:3])[CH3:2].C(N(CC)CC)C>C(Cl)Cl>[C:1]([O:4][CH:5]([CH2:41][O:42][C:43](=[O:45])[CH3:44])[CH2:6][NH:7][C:8]([C:10]1[C:15]([I:16])=[C:14]([N:17]2[CH2:22][CH2:23][CH2:24][CH:20]([OH:21])[C:18]2=[O:19])[C:13]([I:25])=[C:12]([C:26]([NH:28][CH2:29][CH:30]([O:36][C:37](=[O:39])[CH3:38])[CH2:31][O:32][C:33](=[O:35])[CH3:34])=[O:27])[C:11]=1[I:40])=[O:9])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 10920154HCID 10920154, compound

Product 1

HCID 19048401HCID 19048401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of N,N'-bis[2,3-bis(acetyloxy)propyl]-2,4,6-triiodo-5-[[(tetrahydro-2-furanyl)carbonyl]amino]-1,3-benzenedicarboxamide (0.25 g, 0.26 mmol) (the title compound of Example 19) in dry CH2Cl2 (5 mL) was added triethyl amine (0.01 mL). The solution was cooled to 0°-5°, and to this was added dropwise a solution of dimethylboron bromide in CH2Cl2 (0.12 g, 0.5 mL/2 mMol solution in CH2CL2). After stirring the mixture at 0°-5° for 6-8 hours, the mixture was added to a vigorously stirred solution of aqueous saturated sodium bicarbonate (5 mL). After stirring for 5 minutes, ethyl acetate (50 mL) and water (10 mL) were added. The organic layer was separated, washed with water, dried over anhydrous sodium sulfate, and concentrated in vacua to yield the omega-bromo-alpha-hydroxypentanoyl anilide as an off-white fluffy solid (260 mg).

Sources & evidence

ORD record
ord-902057af650f4b17b5008aef24a509fb
Source dataset
uspto-grants-1997_01
Patent number
US05591846

Reaction notes

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