Methanol → (4R)-1-Boc-4-(Boc-amino)-L-proline

HRID 2185410Notes

Reaction equation

HRID 2185410 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:27])[C@@H:7]1[CH2:11][C@@H:10]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:9][N:8]1[C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].CO>O.O1CCCC1>[C:23]([O:22][C:20]([N:8]1[CH2:9][C@H:10]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:11][C@H:7]1[C:6]([OH:27])=[O:5])=[O:21])([CH3:26])([CH3:25])[CH3:24]

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrateHCID 21341546N-tert-butoxycarbonyl-trans-4-(tert-butoxycarbonylamino)-L-proline methyl ester

Product 1

HCID 21341545(4R)-1-Boc-4-(Boc-amino)-L-prolineYield 39.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of lithium hydroxide monohydrate (86 mg) in water (7 mL) was added to a cold (0° C.) stirred solution of N-tert-butoxycarbonyl-trans-4-(tert-butoxycarbonylamino)-L-proline methyl ester (N, 589 mg) in tetrahydrofuran (21 mL)-methanol (7 mL). The mixture was stirred at room temperature for 5 hr and evaporated in vacuo. The residue was diluted with water and washed with ether. The aqueous layer was acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated in vacuo to give the title compound (222 mg) as a colorless foam: 1H NMR (400 MHz, CDCl3) δ 1.35-1.57 (m, 18H), 2.05-2.52 (m, 2H), 3.19-3.37 (m, 1H), 3.66-3.81 (m, 1H, 4.17-4.45 (m, 2H), and 4.63-4.87 (m, 1H).

Workup

  1. customevaporated in vacuo
  2. additionThe residue was diluted with water
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-c0e1e2b988f0475197f8af7c1ddcf09f
Source dataset
uspto-grants-2002_06
Patent number
US06399629B1

Reaction notes

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