Sodium Hydroxide → 1298053-61-8

HRID 1526752Notes

Reaction equation

HRID 1526752 reaction equation
[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([C:54]3[S:58][CH:57]=[C:56]([CH:59]([CH3:61])[CH3:60])[N:55]=3)[CH:10]=[C:11]([O:12][C@H:13]3[CH2:33][N:32]4[C@H:15]([C:16]([NH:18][C@@:19]5([C:45]([NH:47][S:48]([CH:51]6[CH2:53][CH2:52]6)(=[O:50])=[O:49])=[O:46])[C@H:21]([CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]([CH2:34][C:35]([N:37]6[CH2:42][C:41]([F:44])([F:43])[CH2:40][CH2:39][CH2:38]6)=[O:36])[C:30]4=[O:31])[CH2:20]5)=[O:17])[CH2:14]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:62][CH3:63].[OH-].[Na+:65]>CO>[CH3:1][C:2]1[C:7]2[N:8]=[C:9]([C:54]3[S:58][CH:57]=[C:56]([CH:59]([CH3:61])[CH3:60])[N:55]=3)[CH:10]=[C:11]([O:12][C@H:13]3[CH2:33][N:32]4[C@H:15]([C:16]([NH:18][C@@:19]5([C:45]([N-:47][S:48]([CH:51]6[CH2:52][CH2:53]6)(=[O:49])=[O:50])=[O:46])[C@H:21]([CH:22]=[CH:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C@H:29]([CH2:34][C:35]([N:37]6[CH2:42][C:41]([F:44])([F:43])[CH2:40][CH2:39][CH2:38]6)=[O:36])[C:30]4=[O:31])[CH2:20]5)=[O:17])[CH2:14]3)[C:6]=2[CH:5]=[CH:4][C:3]=1[O:62][CH3:63].[Na+:65]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 56935739Deldeprevir

Product 1

HCID 569562521298053-61-8

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound 31 (1 equivalent) was dissolved in dichloromethane, cooled to 5° C. and trifluoroacetic acid (2-3 w/v) was added and stirred at room temperature for 4h. The reaction mixture was concentrated and the residue dissolved in dimethylfomamide and cooled to 5° C. before addition of diisopropylethyl amine (10 equivalents). TBTU (1.8 equivalents) was added followed by 3,3-difluoropiperidine hydrochloride (1.2 equivalents). The reaction was stirred until completion and added to 1M citric acid and solid collected by filtration. The solid was crystallized from ethylacetate/heptane to give ACH-0142684 (purity >98%). ACH-0142684 was suspended in methanol and aqueous sodium hydroxide (1.05 equivalents) was added at about 5° C. to give a clear solution. The reaction mixture was concentrated to dryness and the residue was stirred with IPA to give crystalline ACH-0142684.Na (Form G). The crystalline ACH-0142684.Na was dissolved in a mixture of methanol/ethyl acetate and the solution was added to pentane. The solid was collected by filtration and dried to give ACH-0142684.Na in the amorphous form (purity >98%).

Workup

  1. customto give a clear solution
  2. concentrationThe reaction mixture was concentrated to dryness

Sources & evidence

ORD record
ord-aa144d49ce9140cb8e774e0286b3901a
Source dataset
uspto-grants-2015_07
Patent number
US09085607B2

Reaction notes

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