Hydrogen Bromide → HCID 178461467, compound

HRID 1447458Notes

Reaction equation

HRID 1447458 reaction equation
C(OC([N:11]1[CH2:18][CH2:17][C@@H:16]([CH3:19])[C@@H:12]1[C:13]([OH:15])=[S:14])=O)C1C=CC=CC=1.Br>C(O)(=O)C>[CH3:19][C@@H:16]1[CH2:17][CH2:18][NH:11][C@H:12]1[C:13]([OH:15])=[S:14]

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 178461470HCID 178461470, compound

Product 1

HCID 178461467HCID 178461467, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.4 g. (0.024 mole) of (trans)-1-benzyloxycarbonyl-3-methylthio-D,L-proline are treated with 45 ml. of 4 N hydrobromic acid in acetic acid. After stirring for one hour at room temperature the solution is dried in vacuo. A small amount of water is added and this is washed twice with ether. The aqueous solution is applied to a column containing 300 ml. of an ion-exchange resin and water is passed through until the eluate is no longer strongly acidic. The product is then eluted with pH 6.5 (aqueous pyridine acetate) buffer. Fractions positive to ninhydrin are combined and lyophilized to give 3.4 g. (88%) of white fluff. A small sample of this material is crystallized from methanol to give (trans)-3-methylthio-D,L-proline; m.p. 196°-200° (dec.) (s. 192°).

Workup

  1. customis dried in vacuo
  2. additionA small amount of water is added
  3. washthis is washed twice with ether
  4. additioncontaining 300 ml
  5. washThe product is then eluted with pH 6.5 (aqueous pyridine acetate) buffer
  6. customto give 3.4 g
  7. customA small sample of this material is crystallized from methanol

Sources & evidence

ORD record
ord-e6ea03bbb2b94e3cbc064d0d745ede8b
Source dataset
uspto-grants-1982_02
Patent number
US04316906

Reaction notes

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