Tetrabutylammonium Fluoride → (1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

HRID 926009Notes

Reaction equation

HRID 926009 reaction equation
[Si]([O:18][C@@H:19]1[CH2:44][CH2:43][C@H:22]2[C:23](=[O:42])[N:24]([CH3:41])[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][C@@H:31]3[CH2:36][C@@:32]3([C:37]([O:39][CH3:40])=[O:38])[NH:33][C:34](=[O:35])[C@@H:21]2[CH2:20]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:18][C@@H:19]1[CH2:44][CH2:43][C@H:22]2[C:23](=[O:42])[N:24]([CH3:41])[CH2:25][CH2:26][CH2:27][CH2:28][CH:29]=[CH:30][C@@H:31]3[CH2:36][C@@:32]3([C:37]([O:39][CH3:40])=[O:38])[NH:33][C:34](=[O:35])[C@@H:21]2[CH2:20]1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 131735010(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-(tert-butyldiphenylsilyloxy)-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

Product 1

HCID 69915043(1aR,3aR,5R,7aR,15aS,Z)-methyl 5-hydroxy-9-methyl-3,8-dioxo-1a,2,3,3a,4,5,6,7,7a,8,9,10,11,12,13,15a-hexadecahydro-1H-benzo[c]cyclopropa[g][1,6]diazacyclotetradecine-1a-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of compound 42 (0.6 mmol) in dry THF (12 mL) was added dropwise a solution of tetrabutylammonium fluoride (1M in THF, 12 mL). The reaction was stirred at room temperature overnight, and then concentrated. The residue was dissolved in MeOH and purified by semi preparative HPLC (RP18) to yield compound 43, which was used without further purification directly in the next step. MS (ESI, EI+): m/z=379 (MH+).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in MeOH
  3. custompurified by semi preparative HPLC (RP18)

Sources & evidence

ORD record
ord-eb5f664767214c3197153e4dbb6ab6ee
Source dataset
uspto-grants-2016_03
Patent number
US09284307B2

Reaction notes

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