Methanol → (2S,4R)-4-(4-Bromobenzyloxy)-2-methyl-proline Methyl Ester

HRID 49980

Reaction equation

HRID 49980 reaction equation
O=S(Cl)Cl.C([N:12]1[CH2:19][C@H:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[CH2:17][C@@:13]1([CH3:29])[C:14]([OH:16])=[O:15])(OC(C)(C)C)=O.[CH3:30]O>>[CH3:30][O:16][C:14](=[O:15])[C@:13]1([CH3:29])[CH2:17][C@@H:18]([O:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([Br:28])=[CH:24][CH:23]=2)[CH2:19][NH:12]1

Participants

4

Reactant 3

HCID 887Methanol2×HCID 24386Thionyl ChlorideHCID 21301005(2S,4R)-N-Boc-4-(4-Bromobenzyloxy)-2-methyl-proline

Product 1

HCID 59917097(2S,4R)-4-(4-Bromobenzyloxy)-2-methyl-proline Methyl Ester

Conditions

Temperature
20 °C

Procedure

SOCl2 (0.27 mL) was carefully added dropwise to 2.7 mL of MeOH at −5° C. To this mixture was added (2S,4R)-N-Boc-4-(4-Bromobenzyloxy)-2-methyl-proline (0.25 g) in 2.7 mL of MeOH. The reaction mixture was allowed to warm to 20° C. and stirred overnight. The solvent was evaporated under reduced pressure and the residue dissolved in DCM. The organic layer was washed with water, dried over MgSO4, and evaporated in vacuo to afford the titled compound (85 mg).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionthe residue dissolved in DCM
  3. washThe organic layer was washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-b910daef01354485a9900e65aeddd66b
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Linked notes

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