Hydrogen Bromide → HCID 70374174, compound

HRID 1733346Notes

Reaction equation

HRID 1733346 reaction equation
C([N:11]1[CH2:18][C@@H:17]([F:19])[CH2:16][C@H:12]1[C:13]([OH:15])=[O:14])(OCC1C=CC=CC=1)=O.[BrH:20].CCOCC>C(O)(=O)C>[BrH:20].[F:19][C@@H:17]1[CH2:18][NH:11][C@H:12]([C:13]([OH:15])=[O:14])[CH2:16]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 3283Diethyl EtherHCID 11708768HCID 11708768, compound

Product 1

HCID 70374174HCID 70374174, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The cis-N-carbobenzyloxy-4-fluoro-L-proline (5.5 g., 0.021 mole) is treated with 28 ml. of hydrogen bromide in acetic acid (30-32%), stoppered loosely, and stirred for one hour. Ether (300 ml.) is added to the yellow mixture and when the crystalline product has settled the ethereal liquor is decanted and the material washed with 300 ml. of fresh ether by decantation. The product is finally heated in the steam bath with 70 ml. of methyl ethyl ketone, cooled for two hours, washed with cold methyl ethyl ketone and with ether, and dried in vacuo. The yield of nearly colorless solid, cis-4-fluoro-L-proline, hydrobromide is 3.8 g. (86%), m.p. 189°-191° (dec.), [α]D26 -19° (c=1, methanol).

Workup

  1. customis decanted
  2. washthe material washed with 300 ml
  3. temperatureThe product is finally heated in the steam bath with 70 ml
  4. temperatureof methyl ethyl ketone, cooled for two hours
  5. washwashed with cold methyl ethyl ketone and with ether
  6. customdried in vacuo

Sources & evidence

ORD record
ord-85b8d792bc3f4940b27ef1b890ca58f5
Source dataset
uspto-grants-1980_12
Patent number
US04241076

Reaction notes

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