Diisopropylethylamine → HCID 58573270, compound

HRID 931948Notes

Reaction equation

HRID 931948 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]2[N:8](CO)[C:9](=[O:32])[C@:10]3([C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C@H:13]([CH2:23][C:24]([OH:26])=[O:25])[C:12](=[O:27])[N:11]3[CH2:28][CH:29]3[CH2:31][CH2:30]3)[C:5]2=[CH:4][CH:3]=1.CCN(C(C)C)C(C)C>CO>[Cl:1][C:2]1[CH:7]=[C:6]2[NH:8][C:9](=[O:32])[C@:10]3([C@@H:15]([C:16]4[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=4)[CH2:14][C@H:13]([CH2:23][C:24]([OH:26])=[O:25])[C:12](=[O:27])[N:11]3[CH2:28][CH:29]3[CH2:31][CH2:30]3)[C:5]2=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 58573478HCID 58573478, compound

Product 1

HCID 58573270HCID 58573270, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (rac) 2-((2′S,3′R,5′R)-6-chloro-3′-(3-chlorophenyl)-1′-(cyclopropylmethyl)-1-(hydroxymethyl)-2,6′-dioxospiro[indoline-3,2′-piperidine]-5′-yl)acetic acid (Example 62, Step L) (12.6 mg, 0.025 mmol) in MeOH (1 mL) at room temperature was added DIEA (8.74 μL, 0.050 mmol). The reaction mixture was stirred at room temperature for 1 h. The reaction was quenched with 10% citric acid and concentrated under reduced pressure. The residue was purified by reversed phase preparatory HPLC (column: Gemini-NX C18 5 um column; Phenomonex, Torrance, Calif.; eluent: 0 to 100% MeCN +0.1% TFA in water +0.1% TFA) to give the title compound.

Workup

  1. customThe reaction was quenched with 10% citric acid
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by reversed phase preparatory HPLC (column: Gemini-NX C18 5 um column; Phenomonex, Torrance, Calif.; eluent: 0 to 100% MeCN +0.1% TFA in water +0.1% TFA)

Sources & evidence

ORD record
ord-3f13d7238f864c6b9ca0c521cabfdd9b
Source dataset
uspto-grants-2016_03
Patent number
US09296736B2

Reaction notes

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