Diisopropylethylamine → HCID 86758838, compound

HRID 1058861Notes

Reaction equation

HRID 1058861 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@H:9]([NH:13][C:14]2[C:17](=[O:18])[C:16](=[O:19])[C:15]=2[NH:20][CH2:21][CH2:22][CH3:23])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C.[CH3:33][O:34][C:35]1[C:43]([O:44][CH3:45])=[C:42]([O:46][CH3:47])[CH:41]=[CH:40][C:36]=1[C:37](Cl)=O>C(Cl)Cl>[CH3:33][O:34][C:35]1[C:43]([O:44][CH3:45])=[C:42]([O:46][CH3:47])[CH:41]=[CH:40][C:36]=1[CH2:37][NH:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([NH:13][C:14]2[C:17](=[O:18])[C:16](=[O:19])[C:15]=2[NH:20][CH2:21][CH2:22][CH3:23])[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27608082,3,4-trimethoxybenzoyl chlorideHCID 53829487HCID 53829487, compound

Product 1

HCID 86758838HCID 86758838, compoundYield 0.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the derivatised resin (5), (120 mg) was added DCM (5 ml), DIPEA (0.1 ml, 0.6 mmol) and 2,3,4-trimethoxybenzoyl chloride (138 mg, 0.6 mmol). The solution was agitated for 12 h at RT then filtered and washed thoroughly with DCM. The resin was treated with 60% trifluoroacetic acid in DCM (1.5 ml) for 3 h with agitation and then filtered. The filtrate was evaporated in vacuo to give the crude product which was purified by preparative HPLC to afford the title compound (0.5 mg).

Workup

  1. filtrationthen filtered
  2. washwashed thoroughly with DCM
  3. additionThe resin was treated with 60% trifluoroacetic acid in DCM (1.5 ml) for 3 h with agitation
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. customto give the crude product which
  7. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-b952a01d36294664a3efb15686e827f2
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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