tert-Butyl bromoacetate → HCID 22897435, compound

HRID 1017770Notes

Reaction equation

HRID 1017770 reaction equation
[F:1][C:2]([F:31])([F:30])[C:3]1[CH:4]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([NH:21][CH3:22])[C@@H:17]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH3:14])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Br[CH2:33][C:34]([O:36][C:37](C)(C)C)=[O:35].CCN(C(C)C)C(C)C>C(#N)C>[F:12][C:9]([F:10])([F:11])[C:7]1[CH:6]=[C:5]([C@H:13]([O:15][C@H:16]2[CH2:20][CH2:19][C@@H:18]([N:21]([CH2:33][C:34]([O:36][CH3:37])=[O:35])[CH3:22])[C@@H:17]2[C:23]2[CH:28]=[CH:27][C:26]([F:29])=[CH:25][CH:24]=2)[CH3:14])[CH:4]=[C:3]([C:2]([F:1])([F:30])[F:31])[CH:8]=1

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 22885692HCID 22885692, compound

Product 1

HCID 22897435HCID 22897435, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 251 mg of 1-(S)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)ethoxy)-2-(S)-(4-fluorophenyl)-3-(R)-(methylamino)cyclopentane from Example 15 in 6 mL of acetonitrile was added 0.108 mL of t-butyl bromoacetate and 0.36 mL of DIPEA. The reaction was heated at 50° C. for 5 hours and then concentrated in vacuo. The residue was diluted with water and extracted twice with ethyl acetate. The organic layers were washed with brine, dried with sodium sulfate, combined and evaporated. The residue was purified by FC (0-2.5% methanol in methylene chloride) to afford 294 mg of title compound. Mass spec (ESI): 564 (M+1).

Workup

  1. concentrationconcentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionextracted twice with ethyl acetate
  4. washThe organic layers were washed with brine
  5. dry with materialdried with sodium sulfate
  6. customevaporated
  7. customThe residue was purified by FC (0-2.5% methanol in methylene chloride)

Sources & evidence

ORD record
ord-7e2cf46bf19a47a889fb61e9cfa42d21
Source dataset
uspto-grants-2002_11
Patent number
US06479518B2

Reaction notes

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