Water → benzyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamate

HRID 1354551Notes

Reaction equation

HRID 1354551 reaction equation
[CH2:1]([C@H:3]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([C:13]([F:16])([F:15])[F:14])=[CH:9][CH:8]=2)[C:5](=[O:17])[CH2:4]1)[CH3:2].[C:18](=[O:28])([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[NH2:19].CC(C)([O-])C.[Li+].O1CCCC1.O>O1CCCC1.C(OCC)(=O)C>[F:16][C:13]([F:14])([F:15])[C:10]1[CH:9]=[CH:8][C:7]([NH:6][C@H:3]([CH2:1][CH3:2])[CH2:4][C:5]([NH:19][C:18](=[O:28])[O:20][CH2:21][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)=[O:17])=[CH:12][CH:11]=1

Participants

7

Reactant 4

HCID 962WaterHCID 12136Benzyl carbamateHCID 10105825(R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinoneHCID 86594548HCID 86594548, compound

Product 1

HCID 10178731benzyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamateYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

80.0 mg (0.33 mmol) of (R)-4-ethyl-1-[4-(trifluoromethyl)phenyl]-2-azetidinone produced in Example 6and 74.8 mg (0.50 mmol) of benzyl carbamate were dissolved in tetrahydrofuran (3 mL) and further mixed with a lithium tert-butoxide/tetrahydrofuran solution (1 mol/L, 0.50 mL, 0.50 mmol) at room temperature. After stirring at the same temperature for 1.5 hours, water (5.0 mL) was further added to the reaction solution and extraction with ethyl acetate (5 mL) was repeated three times. The residue obtained by concentrating the separated organic layer dried with anhydrous magnesium sulfate was purified on silica gel column chromatography to obtain benzyl (R)-{3-[4-(trifluoromethyl)phenylamino]-pentanoyl}carbamate as a white solid (112 mg, isolated yield: 86%). 1H-NMR (CDCl3, 400 MHz/ppm): δ 0.98 (3H, t), 1.5-1.8 (2H, m), 2.9-3.2 (2H, m), 3.8-3.9 (1H, m), 4.2-4.3 (1H, br), 5.17 (2H, s), 6.60 (2H, d), 7.3-7.4 (7H, m), 7.5-7.6 (1H, br)

Workup

  1. customThe residue obtained
  2. concentrationby concentrating the separated organic layer
  3. dry with materialdried with anhydrous magnesium sulfate
  4. customwas purified on silica gel column chromatography
  5. customto obtain

Sources & evidence

ORD record
ord-e9a091f3a70241b3b7484f1803ed2528
Source dataset
uspto-grants-2007_05
Patent number
US07223859B2

Reaction notes

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