Ammonium Chloride → HCID 86680898, compound

HRID 2042955Notes

Reaction equation

HRID 2042955 reaction equation
[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34](Cl)=[C:33]([CH2:38][C:39]3[S:40][C:41]([C:44]4[O:45][CH:46]=[CH:47][CH:48]=4)=[CH:42]N=3)[CH:32]=2)[O:11][C@@H:10]1[C:49](OC)=[O:50])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:53]([Mg]Cl)[CH3:54].[NH4+:57].[Cl-:58]>C1COCC1>[CH2:1]([O:8][C@H:9]1[C@H:14]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@@H:13]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[C@H:12]([C:31]2[CH:36]=[CH:35][C:34]([Cl:58])=[C:33]([CH2:38][C:39]3[S:40][C:41]([C:44]4[O:45][CH:46]=[CH:47][CH:48]=4)=[CH:42][N:57]=3)[CH:32]=2)[O:11][C@@H:10]1[C:49]1([OH:50])[CH2:54][CH2:53]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 86680897HCID 86680897, compoundHCID 178461633HCID 178461633, compound

Product 1

HCID 86680898HCID 86680898, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of methyl ester 105 (350 mg, 0.47 mmol) in THF (2.5 mL) was added ethyl magnesiumchloride (1.2 mL, 2.0M solution in THF) and Ti(Oi-Pr)4 (0.15 mL 0.52 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 18 h. The reaction mixture was poured into a saturated NH4Cl solution and extracted with ethyl acetate. The organic layer was dried over anhydrous MgSO4, filtere, and concentrated in vacuo. Purification by silica gel column chromatography provided of desired tertiary alcohol 107 (98 mg, 28%) as a solid. MH+734.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. concentrationfiltere, and concentrated in vacuo
  4. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-14f4095f6cdd4f4da2d6ba708572025e
Source dataset
uspto-grants-2013_11
Patent number
US08586550B2

Reaction notes

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