Hydrochloric Acid → Methyl 3-(S)-(N-(4-methoxybenzyl)-N-(benzyloxycarbonyl)-amino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate

HRID 1289972Notes

Reaction equation

HRID 1289972 reaction equation
[CH3:1][O:2][C:3]1[CH:26]=[CH:25][C:6]([CH2:7][NH:8][C@H:9]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[C@H:10]2[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:5][CH:4]=1.Cl[C:28]([O:30][CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:29].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]([C@H:9]2[CH2:13][CH2:12][C@H:11]([C:14]([O:16][CH3:17])=[O:15])[C@H:10]2[C:18]2[CH:19]=[CH:20][C:21]([F:24])=[CH:22][CH:23]=2)[C:28]([O:30][CH2:31][C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)=[O:29])=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10387Benzyl chloroformateHCID 81531DiisopropylethylamineHCID 22885804methyl 3-(S)-((4-methoxyphenyl)methylamino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate

Product 1

HCID 22885814Methyl 3-(S)-(N-(4-methoxybenzyl)-N-(benzyloxycarbonyl)-amino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.1 g of methyl 3-(S)-(4-methoxybenzyl-amino)-2-(S)-(4-fluorophenyl)cyclopentane-1-(S)-carboxylate, prepared as in Example 61, in 50 mL of methylene chloride was added 1.36 mL of benzyl chloroformate and after 5 min 3.0 mL of DIPEA. After stirring at room temperature for 16 h, the reaction was poured into water containing 3 mL of 2N HCl and was extracted twice with methylene chloride. The organic layers were washed with a portion of brine, combined, dried over sodium sulfate and evaporated. The residue was purified by flash chromatography eluting with 10% ethyl acetate in hexanes to obtain 3.95 g of title compound as an oil. T.l.c. (10% ethyl acetate in hexanes) Rf =0.35

Workup

  1. extractionwas extracted twice with methylene chloride
  2. washThe organic layers were washed with a portion of brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-01405f451e20477dbae9b52e20fedc00
Source dataset
uspto-grants-1998_05
Patent number
US05750549

Reaction notes

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