Hydrochloric Acid → HCID 59697084, compound

HRID 1670169Notes

Reaction equation

HRID 1670169 reaction equation
Cl.[NH2:2][OH:3].C[O-].[Na+].C[O:8][C:9](=O)[C@@H:10]([NH:14][C:15](=[O:24])[C:16]1[CH:21]=[CH:20][C:19]([F:22])=[C:18]([Br:23])[CH:17]=1)[C@H:11]([OH:13])[CH3:12].Cl>CO>[Br:23][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][C:19]=1[F:22])[C:15]([NH:14][C@H:10]([C:9]([NH:2][OH:3])=[O:8])[C@H:11]([OH:13])[CH3:12])=[O:24]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 59697181HCID 59697181, compound

Product 1

HCID 59697084HCID 59697084, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of hydroxylamine hydrochloride (66 mg, 0.95 mmol) in anhydrous MeOH (2.0 mL) at 0° C. under N2 atmosphere was added sodium methoxide (25 wt % in MeOH, 360 mg, 1.67 mmol). A precipitate formed immediately and the cloudy white solution was stirred for 10 minutes at 0° C. A solution of methyl (2S,3R)-2-[(3-bromo-4-fluorophenyl)carbonylamino]-3-hydroxybutanoate (2) (284 mg, 0.850 mmol) in MeOH (2.0 mL) was added and the reaction stirred 2 h at 0° C. and then warmed gradually to room temperature overnight (17 h total). Aqueous 1.0 M HCl (10 mL) was added and the solution extracted with 4:1 chloroform/isopropyl alcohol (4×20 mL). The organic layers were combined, dried over Na2SO4 and concentrated to give a pink foam. The crude solid was triturated with diethyl ether (2×8 mL) and dried in vacuo to give 3-bromo-4-fluoro-N-{(1S,2R)-2-hydroxy-1-[(hydroxyamino)carbonyl]propyl}benzamide 3 as a white foam: mp 152-153° C. Rf (10:1 CH2Cl2/MeOH on silica gel)=0.53.

Workup

  1. customA precipitate formed immediately
  2. stirringthe reaction stirred 2 h at 0° C.
  3. temperaturewarmed gradually to room temperature overnight (17 h total)
  4. extractionthe solution extracted with 4:1 chloroform/isopropyl alcohol (4×20 mL)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give a pink foam
  8. customThe crude solid was triturated with diethyl ether (2×8 mL)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-c06b2651ba2146a69bd5866b717d6ca2
Source dataset
uspto-grants-2011_08
Patent number
US07989660B2

Reaction notes

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