Methanol → Trans-4-(4-bromo-benzyloxy)-L-proline Methyl Ester

HRID 49969Notes

Reaction equation

HRID 49969 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@H:13]1[C:14]([OH:16])=[O:15])(OC(C)(C)C)=O.[CH3:29]O>>[CH3:29][O:16][C:14](=[O:15])[C@@H:13]1[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 21301025trans-N-Boc-4-(4-bromo-benzyloxy)-L-proline

Product 1

HCID 69891171Trans-4-(4-bromo-benzyloxy)-L-proline Methyl Ester

Conditions

Temperature
20 °C

Procedure

SOCl2 (0.27) was carefully added dropwise to 2.7 mL of MeOH at −5° C. To this mixture was added trans-N-Boc-4-(4-bromo-benzyloxy)-L-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 above-titled compound (60 mg). NMR (CDCl3, 200 MHz): 7.45 (2H, d), 7.2 (2H, d), 4.44 (2H, s), 4.15-4.05 (1H, m), 4.0 (1H, t), 3.7 (3H, s), 3.2-3.05 (2H,m), 2.27 (1H, dd), 2.05-1.9 (1H, m).

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-9d8c3d17f54d4cb99215707ff07018e0
Source dataset
uspto-grants-2004_03
Patent number
US06710064B2

Reaction notes

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