Diisopropylethylamine → Methyl (S)-2-[(8-azaspiro[4.5]decane-8-carbonyl)amino]-4,4-difluoro-5-phenylpentanoate

HRID 1664718Notes

Reaction equation

HRID 1664718 reaction equation
[F:1][C:2]([F:19])([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:3][C@H:4]([N:9]=[C:10]=[O:11])[C:5]([O:7][CH3:8])=[O:6].[CH2:20]1[C:24]2([CH2:29][CH2:28][NH:27][CH2:26][CH2:25]2)[CH2:23][CH2:22][CH2:21]1.CCN(C(C)C)C(C)C>ClCCl>[CH2:23]1[C:24]2([CH2:29][CH2:28][N:27]([C:10]([NH:9][C@@H:4]([CH2:3][C:2]([F:19])([F:1])[CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)[C:5]([O:7][CH3:8])=[O:6])=[O:11])[CH2:26][CH2:25]2)[CH2:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 4371528-Azaspiro(4.5)decaneHCID 86635603Methyl (S)-4,4-difluoro-2-isocyanato-5-phenylpentanoate

Product 1

HCID 66661189Methyl (S)-2-[(8-azaspiro[4.5]decane-8-carbonyl)amino]-4,4-difluoro-5-phenylpentanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Methyl (S)-4,4-difluoro-2-isocyanato-5-phenylpentanoate (425 mg, 1.58 mmol) were dissolved in 25 ml of dichloromethane. 8-Azaspiro[4.5]decane (220 mg, 1.58 mmol, 1 eq.) and DIPEA (269 μl, 204 mg, 1.58 mmol, 1 eq.) were added to this solution which was stirred at RT overnight. The solvent was removed under reduced pressure and the residue was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA). The product-containing fractions were combined and freed from the solvent under reduced pressure.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by preparative HPLC (gradient: acetonitrile/water and addition of 0.05% TFA)

Sources & evidence

ORD record
ord-06329d881efd4c3eb816ce32a14584cd
Source dataset
uspto-grants-2011_10
Patent number
US08039480B2

Reaction notes

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