Dichloromethane → HCID 86719335, compound

HRID 1776482Notes

Reaction equation

HRID 1776482 reaction equation
[CH:1]1[C:13]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19](CCOC(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:20]([O:22][C@H:23]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]4[CH2:48][CH2:47]4)[CH:35]=3)[CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27]C=3Cl)=[O:21])=[O:17])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[OH2:71].[CH3:72][C:73]1[CH:78]=CC(S(O)(=O)=O)=CC=1.[CH2:83]([Cl:85])Cl>>[CH:10]1[C:11]2[CH:12]([CH2:14][O:15][C:16]([NH:18][C@H:19]([CH2:72][CH2:73][CH2:78][OH:71])[C:20]([O:22][C@H:23]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]4[CH2:48][CH2:47]4)[CH:35]=3)[CH2:24][C:25]3[C:30]([Cl:31])=[CH:29][N+:28]([O-:32])=[CH:27][C:83]=3[Cl:85])=[O:21])=[O:17])[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 3

HCID 6344Dichloromethane2×HCID 521998p-Toluenesulfonic acid monohydrateHCID 86719336HCID 86719336, compound

Product 1

HCID 86719335HCID 86719335, compound

Procedure

To a solution of 4-((S)-2-((R)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-4-(trityloxy)butanoyloxy)-2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)-phenyl)ethyl)-3,5-dichloropyridine 1-oxide (354 mg, 0.354 mmol) in DCM (5 mL), 4-methylbenzenesulfonic acid hydrate (14 mg, 0.071 mmol) was added. The mixture was stirred at room RT overnight. The mixture was then diluted with DCM and washed with NaHCO3 sat. sol. The organic phase was dried over Na2SO4, and the solvent was evaporated, to yield 268 mg of the title compound.

Workup

  1. washwashed with NaHCO3 sat. sol. The organic phase
  2. dry with materialwas dried over Na2SO4
  3. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d0901a18531b48d2a1c4cfe776eac47b
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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