Ammonium fluoride → HCID 57978218, compound

HRID 1866523Notes

Reaction equation

HRID 1866523 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([O:31][Si](C(C)(C)C)(C)C)[CH2:16][NH:17][C@H:18]([CH3:30])[CH2:19][C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[CH:11][C:10]=1[CH2:39][OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F-].[NH4+]>CO.O>[NH3:17].[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C@@H:15]([OH:31])[CH2:16][NH:17][C@H:18]([CH3:30])[CH2:19][C:20]2[CH:21]=[C:22]([CH:27]=[CH:28][CH:29]=2)[C:23]([O:25][CH3:26])=[O:24])=[CH:11][C:10]=1[CH2:39][OH:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 25516Ammonium fluorideHCID 57978348HCID 57978348, compound

Product 2

HCID 222AmmoniaHCID 57978218HCID 57978218, compoundYield 171.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 3-{(2R)-2-[((2R)-2-[4-(benzyloxy)-3-(hydroxymethyl)phenyl]-2-{[tert-butyl(dimethyl)silyl]oxy}ethyl)amino]propyl}benzoate (Preparation 62) (10 g, 17.74 mmol) and ammonium fluoride (6.57 g, 177 mmol) in methanol (180 ml) and water (60 ml) was heated at 40° C. for 18 hrs. The methanol was removed in vacuo and the remaining aqueous layer extracted with dichloromethane (2×100 ml). The combined organic layers were dried (sodium sulfate), filtered and evaporated in vacuo. The resulting oil was purified by flash column chromatography on silica gel eluting with dichloromethane:methanol:880 ammonia (95:5:0.5, by volume) to give the title compound (6.83 g) as a pale yellow gum. 1H NMR (400 MHz, CD3OD): δ=7.83-7.82 (1H, d), 7.78 (1H, s), 7.47-7.45 (2H, m), 7.39-7.28 (6H, m), 7.11-7.10 (1H, d), 6.89-6.87 (1H, d), 5.11 (2H, s), 4.65 (2H, s), 4.65-4.62 (1H, m), 3.88 (3H, s), 2.98-2.89 (2H, m), 2.79-2.64 (3H, m), 1.09-1.08 (3H, d) ppm. LRMS (electrospray): m/z [M+H]+ 450, [M+Na]+ 472, [M−H]− 448.

Workup

  1. customThe methanol was removed in vacuo
  2. extractionthe remaining aqueous layer extracted with dichloromethane (2×100 ml)
  3. dry with materialThe combined organic layers were dried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe resulting oil was purified by flash column chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-b1aa8bc91db44fe98b284e1f2ab44f79
Source dataset
uspto-grants-2009_12
Patent number
US07629358B2

Reaction notes

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