Hydrochloric Acid → HCID 86606737, compound

HRID 1433327Notes

Reaction equation

HRID 1433327 reaction equation
[OH:1][CH2:2][C@@:3]([NH:24]C(=O)OC(C)(C)C)([CH3:23])[CH2:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH2:14][CH2:15][C:16]([F:22])([F:21])[C:17]([F:20])([F:19])[F:18])=[CH:8][CH:7]=1.[ClH:32]>O1CCOCC1>[ClH:32].[NH2:24][C@:3]([CH3:23])([CH2:4][CH2:5][C:6]1[CH:7]=[CH:8][C:9]([O:12][CH2:13][CH2:14][CH2:15][C:16]([F:21])([F:22])[C:17]([F:18])([F:19])[F:20])=[CH:10][CH:11]=1)[CH2:2][OH:1]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86606738HCID 86606738, compound

Product 1

HCID 86606737HCID 86606737, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To tert-butyl {(R)-1-hydroxy-2-methyl-4-[4-(4,4,5,5,5-pentafluoro-pentyloxy)-phenyl]-but-2-yl}-carbamate (25 mg, 0.055 mmol) is added 4 M HCl in dry dioxane (1 ml). The clear colorless solution is stirred for 2 h protected from moisture. Then, the solution is evaporated to dryness and the partially crystalline residue is taken up in dry ether (5 ml). Sonication for 10 min gives a precipitate of colorless crystals. The product is filtered off, washed with cold ether (3×1 ml), and dried in vacuo to afford the title compound in form of a non hygroscopic colorless microcrystalline powder: mp. 186-189° C. MS (ESI+): 356 (MH+), 1H-NMR (400 MHz, CD3OD): δ 1.35 (s, 3H, 2-Me), 1.91 (cm, 2H, 3-CH2), 2.06 (cm, 2H, 2′-CH2), 2.35 (cm, 2H, 3′-CH2), 2.63 (cm, 2H, 4-ArCH2), 3.55 (d, 1H, 2J=12.1, 1-CHα), 3.63 (d, 1H, 2J=11.9, 1-CHβ), 4.06 (t, 3H, 3J=7.1, 1′-OCH2), 6.88 (‘d’, 2H, J=11.0, ArH), 7.18 (‘d’, J=10.8 Hz, ArH).

Workup

  1. customThen, the solution is evaporated to dryness
  2. customSonication for 10 min
  3. customgives a precipitate of colorless crystals
  4. filtrationThe product is filtered off
  5. washwashed with cold ether (3×1 ml)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-617c0c7034a84188af7ee771cfb9e1ee
Source dataset
uspto-grants-2009_11
Patent number
US07612238B2

Reaction notes

Loading…