1,4-Dioxane → HCID 86758839, compound

HRID 1058862Notes

Reaction equation

HRID 1058862 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.O1CCOCC1.CCN(C(C)C)C(C)C.[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][C:48](Cl)=[O:49])=[CH:43][CH:42]=1>O>[CH3:39][O:40][C:41]1[CH:46]=[CH:45][C:44]([O:47][C:48]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([CH2:8][C@H:9]([NH:13][C:14]3[C:17](=[O:18])[C:16](=[O:19])[C:15]=3[NH:20][CH2:21][CH2:22][CH3:23])[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=2)=[O:49])=[CH:43][CH:42]=1

Participants

6

Reactant 4

HCID 312751,4-DioxaneHCID 81531DiisopropylethylamineHCID 82128Carbonochloridic acid, 4-methoxyphenyl esterHCID 53829487HCID 53829487, compound

Product 1

HCID 86758839HCID 86758839, compoundYield 1.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To the derivatised resin (5), (120 mg) was added 1,4-dioxan (4.5 ml), DIPEA (0.2 ml, 1.2 mmol), water (0.5 ml) and 4-methoxyphenylchloroformate (0.2 ml, 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 (2 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-9a0a2fb647e2463c939f90a0942ae8ec
Source dataset
uspto-grants-2003_02
Patent number
US06518283B1

Reaction notes

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