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1,2-Dichloroethane → HCID 86679523, compound

HRID 1776567
Notes
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Reaction equation

HRID 1776567 reaction equation
[C:1]([S:4][C:5]([CH3:19])([CH3:18])[CH:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7]([OH:9])=[O:8])(=[O:3])[CH3:2].C(Cl)CCl.[Cl:24][C:25]1[CH:26]=[N+:27]([O-:50])[CH:28]=[C:29]([Cl:49])[C:30]=1[CH2:31][C@@H:32]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:43])[F:42])=[C:36]([O:44][CH2:45][CH:46]2[CH2:48][CH2:47]2)[CH:35]=1)O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]([S:4][C:5]([CH3:19])([CH3:18])[CH:6]([NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7]([O:9][C@H:32]([C:34]1[CH:39]=[CH:38][C:37]([O:40][CH:41]([F:42])[F:43])=[C:36]([O:44][CH2:45][CH:46]2[CH2:47][CH2:48]2)[CH:35]=1)[CH2:31][C:30]1[C:29]([Cl:49])=[CH:28][N+:27]([O-:50])=[CH:26][C:25]=1[Cl:24])=[O:8])(=[O:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 71092687(S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxideHCID 86679522HCID 86679522, compound

Product 1

HCID 86679523HCID 86679523, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridine
Catalyst
HCID 6344DichloromethaneSolvent2×

Procedure

3-(acetylthio)-2-(tert-butoxycarbonylamino)-3-methylbutanoic acid (693 mg, 2.38 mmol) was dissolved in DCM (10 ml). DMAP (73 mg, 0.59 mmol), EDC (342 mg, 1.79 mmol), and (S)-3,5-dichloro-4-(2-(3-(cyclopropylmethoxy)-4-(difluoromethoxy)phenyl)-2-hydroxyethyl)pyridine 1-oxide (500 mg, 1.19 mmol) were added, and the mixture stirred for 4 hours at RT. The reaction mixture was diluted with DCM and washed with NaHCO3 sat. sol. (10 ml), HCl 1N, brine, dried over Na2SO4 and evaporated under vacuum to give 1.06 g. Crude compound was used in the next step without further purification.

Workup

  1. washwashed with NaHCO3 sat. sol. (10 ml), HCl 1N, brine
  2. dry with materialdried over Na2SO4
  3. customevaporated under vacuum
  4. customto give 1.06 g
  5. customCrude compound was used in the next step without further purification

Sources & evidence

ORD record
ord-aa41d035705c43489f8e52f6090d4ff1
Source dataset
uspto-grants-2016_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09265768B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes